Chestertown; An Architecural Guide


alt For all who have had the pleasure of strolling along Chestertown's ancient High Street, or enjoying its spacious sidewalks lined with tidy brick buildings varied here and there with interesting frame structures - there must inevitably arise the question, how did such a pleasant, workable, and utterly humane plan for town life come into being?

The seat of the Eastern Shore's oldest county Kent was finally put at its present location on the Chester River in 1706. Beginning with a Governor's proclamation in 1668, there had been intermittent proposals to establish a colonial port at about this spot on the river. Doubtless the building of a county court house on the present grounds by 1697 all but assured the founding of the town. Faulty provisions for the sale of the land and other setbacks caused the Legislature in 1730 to order a careful surveying of the Town's 100 acres and the laying out of the logical and functional plan which we continue to enjoy to this day.

A broad main street (called High, platted at 90 feet wide) takes one from the River to the chief public space, situated at the intersection of a crossing street (called Cross, platted at 66 feet wide), where the places of public business and other amenities are located. The simplicity of this scheme (somewhat like a miniaturized Philadelphia) is something of a rarity among Chesapeake ports. Other Chesapeake harbors, like Annapolis and Oxford, being closer to the Bay itself, have too uneven a coastline or irregular a terrain to permit a clear crossplan with neat rectangular subdivisions.

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Besides its court house, the development of Chestertown during the 18th century owed a great deal to its being designated a Port of Entry, becoming an educational center (especially with the founding of Washington College in 1782) and its being a trading center for the vital agricultural industry of the county. The economy down to 1760 had been highly dependent on tobacco, but a dramatic shift in the direction of wheat production brought about a new prosperity that resulted in increased population for the Town and significant new ties with Philadelphia in the period just preceding the Revolution.

After a post-Revolutionary period of decline and relative stagnation, the Town's fortunes clearly began to rise again by 1860, the time when the existing Court House was built. Census figures from 1860 to 1900 show a doubling of the population (to 3008, about 300 people fewer than the present-day count). Fruit growing and the coming of the railroad to Town in 1872 partially account for this small boom, which in turn helps explain the large number of buildings remaining from that period. The 20th century has seen modest growth within the town limits with little architectural change in the Historic District since the reconstruction of a commercial block, destroyed by fire in 1910. Rather, the approach of recent generations has been to preserve the old or to add and replace in architectural styles compatible with the Town's past.

The modern-day visitor will probably be aware that the Town's physical aspect has been noticeably affected by the disappearance of the commercial wharves that once served sail and steam boats in their trade with the outside world. Less obvious perhaps are the changes undergone within the public space at the center of Town. Where there is now a delightful park with its ornate fountain, there stood until the 1890's a solidly built market house, the armory, and the first engine house for the volunteer fire department. The public area around Emmanuel Episcopal Church underwent less drastic change; but it is worth noting that the building of the 1860 court house led not only to the demolition of the clerk's office and the removal of the church cemetery, but to a new and much larger jail (1884) and the development of the row of tiny-scaled lawyer's offices along Court Street. Little realized is the fact that the 18th-century court house formerly faced this street, rather than High, thus explaining the unexpected stateliness of the Geddes-Piper house on nearby Church Alley.

To understand the past appearance of Chestertown's civic center, one must also imagine a grouping of commercial taverns, inns, and hotels around the perimeter; and, just as importantly, a rectangle of open space, 160 feet wide, extending from Court Street to Spring Avenue. An unmistakable axis had been gradually established by the long front of Emmanuel Church, and the later placement of the first Methodist meeting house and the Masonic temple. This provided a northern boundary for an open area which could be used for all sorts of activities: everyday, festive or solemn.

The range of architectural styles to be covered in this brief guide will begin with the "Georgian," so called because this orderly style was favored in the English speaking world during the reigns of the successive kings of that name. In conservative Chestertown, the style remained popular until at least 1830 and it was revived by 1900. The quality of the workmanship in several Chestertown buildings from just before and after the Revolution is notable. The all-header bond brickwork in some important structures (frequently just the facades) was, for example, costly and difficult to execute. Only Annapolis has more buildings in this technique, but this possible close link with the capital city is counter balanced during the Georgian period by clear connections with Philadelphia. Chestertown's largest Georgian building, Washington College, was built by Philadelphia workmen in the 1780's. On the other hand, there must have been good, purely local talent at about this time, for we know of four silversmiths during the 1770's.The romantic movement begins to affect local architecture only by the 1840's, and, it would seem, very conservatively at first. There is little evidence of Downing's version of American Gothic and little to represent the Greek Revival, Very popular by mid-century, however, was the Italianate, or bracketed villa, style. A host of subdued examples of this type of building will be found, both public and private, until the 1870's and 80's when various extreme forms of Gothic or "Queen Anne" make their appearance. Often associated with Queen Victoria's reign, these styles had contemporary vogue in England, and were made possible in Chestertown partly because many of the constituent parts could be ordered ready-made from Baltimore.

All the same, some of the best of the Town's high style architecture dates from this period with no little of the credit due to local builders, like Walter T. Pippin, H. M. Stuart and A. M. Culp. Another popular late l9th century style was the French-inspired Second Empire, seen most impressively in Stam's Hall, one of the Town's best-loved structures. With his house on Washington Avenue, Stam also initiated an expansion of the Town in the direction of the College, that has continued unabated down to our own time. The architectural flair of his own buildings has been reined in considerably since his day, as the beginning of the new century brought more and more conservatism of style and detail. The bungalow of the 1920's represented something of an innovation, but, by and large, the architecture of the 20th century within the Town's Historic District has maintained a sense of continuity with the Town's past. It is perhaps for this reason that visitors and townsmen alike find the place so harmonious and livable today.

plaque.jpg (5137 bytes) This guide presents a sampling of highlights from all eras of Chestertown's architecture. Not every building of merit could be included. The thought has been that a visitor with little time might explore one or two of the four sectors into which the District has been subdivided, leaving for another occasion the viewing of the rest. It is to be hoped that visitors, no matter what length their stay, will recognize that the architectural heritage of the Town is proudly cherished by its citizenry.

Robert J.H. Janson-La Palme Chairman, Historic District Commission

Map of Chestertown's Historic District



Cusatom House Chestertown Maryland1. This handsome 18th-century brick building signalizes Chestertown's importance as a Port of Entry for Maryland's Eastern Shore, one of just six in the colony created by the Maryland General Assembly under pressure from the Crown in 1706. Early buildings of this type and size have all but disappeared from the original 13 colonies. The principal block facing Water Street (originally Front) Street was constructed in the 1740's by Samuel Massey and features Flemish bond brickwork with glazed headers. The prestigious Ringgold family took over the building in the latter part of the 18th century and is presumed responsible for the two-bay addition that is easily detected along the landing front. Although the front porch is a recent reconstruction based on the discovery of footings and other evidence, the porch facing the river is modern. The Custom House has been in private hands for many generations and has been gradually restored in recent years. The graceful front portico is the design of restoration consultant Michael Bourne and uses motifs of the area. This historic building was very important to the establishment of the Town's National Landmark District. Chestertown had a "tea party" in May, 1774, not far away, when a band of angry citizens attacked the cargo aboard the brigantine belonging to Custom Collector William Geddes.

2.A splendid example of the Italianate style that was widely popular in the region, James Taylor built this river-front mansion in 1857. Scrupulously restored, this house retains its finely detailed lantern on its, typically, low-pitched roof and displays a rich series of ornamental brackets under the eaves of both main roof and porches. Fine too are the jig-saw cut porch balustrades and the general proportioning of the building. Key to the appreciation of this type of house design is the combination of symmetry and an open, airy feeling.

3.This impressive brick residence has dominated an important waterfront Street corner for more than two centuries. The compact massing of its all-header and Flemish bond brick walls, hipped roof and Greek Revival style portico stands in marked contrast with #2. The L-shaped structure seems to have been put together in stages with the Water Street block having been built shortly after 1743 by Dr. pic3.jpg (5310 bytes)William Murray. Thomas Ringgold, wealthy merchant and Maryland legislator, remodeled and greatly extended this main block after acquiring it in 1767, installing a beautiful paneled parlor in the front section (dated 1771, attributed to the Annapolis designer and woodcarver William Buckland and now transferred to the Baltimore Museum of Art) while putting in a grand staircase to the rear. The fact that only the garden side wall of the entire rear wing is in all-header bond tends to support consultant Michael Bourne's contention that all of the structure at the back is from Ringgold's time. Had there been a preexisting mid-century house to be incorporated, as has been frequently surmised, the costly all-header bond would have been used, almost certainly, in a Cannon Street entrance wall. Besides Ringgold, there have been many other important residents, such as United States Senator James Alfred Pearce, and, more recently, the presidents of Washington College (which now owns and maintains the building). The Hynson-Ringgold House, as it is now called, possesses in addition to its large walled garden a spacious open lot in front which affords an unbroken vista of the Chester River.

pic4.jpg (6876 bytes)4.This imposing Georgian style house enjoys an excellent site at the foot of High Street. it has thus been the residence of locally prominent families, especially the civically active Wickes. Construction was initiated by the Wallis family, and the clean four-square Flemish brick construction fits the generation of building just prior to the Revolution. Subsequent owners added subsidiary buildings at left and perhaps one at right (both now destroyed) and a large garden extending to the rear. The doorway too is of later construction.

pic5.jpg (5515 bytes)5.This well-restored house presents, at first, the appearance of an 1880's three-bay frame dwelling complete with nicely detailed front porch, slender corner pilasters and a bay window for the parlor. There is evidence of late 18th-century ownership of the 2 ½ -storey section, however, which suggests that, like many other house owners during the relatively prosperous 1880's, John Hines sought a more fashionable facade for his old dwelling.
pic6-7.jpg (5142 bytes)6.& 7. Originally a five-bay single residence, possibly built as early as ca. 1743, this building was widened in the early 19th century into a two family home. The break in the brickwork, which in the earlier part is Flemish bond with glazed headers, makes the addition apparent. Noticeable also is the jog of the water table above the basement windows in the older section. The building has been well cared for in recent years and the comfortable front porches appear to be comparatively modern.

pic8.jpg (4814 bytes)8.A small-scale frame survivor from the second quarter of the 18th century, this building delights because of the contrast between the rigidly symmetrical first floor and the uneven arrangement of the second-storey windows. The front wall has beaded clapboard siding, but the end gables are of brick to accommodate the chimneys. The entrance porch was designed by architect James Wollon at the time the structure was restored by the Maryland Historical Trust.

pic9.jpg (5090 bytes)9.Now a double residence, this five-bay house was originally constructed for John Lorain, ca. 1776-1796. The facade arrangement is, therefore, more thoroughly symmetrical than the earlier #8; but, like it, there are two brick end gables framing a front wall of wood. The front porches are from some time in the last century.

pic10.jpg (4703 bytes)10.Built in mid-19th century by Thomas Hynson, this building is in a simplified Italianate style. It retains part of a tell-tale lantern atop its low hipped roof, has a bracketed cornice, and walls of hard brick with fine mortar joints. The large ground-storey windows can be explained by the fact that the old retail district of the Town began at about this point on High Street and that there was definitely a shop here in the later 19th century, probably even from the very beginning.

pic11.jpg (6763 bytes)11. Constructed by the Buck family ca. 1735-50, this building has undergone extensive restoration thanks to Preservation, Inc., a local group, and the Maryland Historical Trust. Like its later counterpart across the street, this brick structure is known to have served as a store, at least in its later life (1854-1922) when in the hands of the Bacchus family. Important in the restoration were: the raising of the roof lines according to evidence uncovered by Michael Bourne, restoration consultant; the reopening of a Queen Street entrance; the relocation of the High Street door; and the design of appropriate doorsteps. A clumsy early 19th-century addition at the right of the High Street front has been appropriately kept, but its common bond brickwork contrasts with the Flemish bond wall, irregular string courses and fieldstone foundation of the early construction. The building serves in part as a small local museum.

12.The Imperial Hotel was erected in 1903 by W. W. Hubbard for use as office and store as well as a place of lodging. The double tiered verandah offers a pleasant aspect from the street and has shaded and sheltered many a passerby on the walk below. The entire building has been renovated for use as a hotel with the harmonious addition of an entrance court at the rear (visible from Queen Street) that includes a rustic outbuilding designed by local architect Marsha Fritz.

13.The Chester Theater opened in 1928 as the New Lyceum. It supplemented Stam's Hall, which became known as the Old Lyceum, as a place of public entertainment. The yellow brick in the front of this building is unusual for the town, though fashionable architects began to use this color by the 1890's elsewhere. Like #23, the street-level doorways are clustered together and placed within a wide frame of bricks in parallel rows. Similarly, there is also the use of a checkerboard pattern of brick in conjunction with the second-storey window arches. Although the ground-storey bricks have been painted, much of the roof and marquee treatment appears to be original.

14.A Chestertown druggist/merchant, Colin Stam, undertook this large and ambitiously designed building in 1886 to house his flourishing business on the ground floor and provide spaces for public entertainment and gatherings on the second and third floors. The people of the town contributed S1,000 to pay for a bell in the tower, which still tolls the hours. The structure is in the Second Empire or Beaux Arts style, that was widely popular during the 1870's and '80's for civic buildings. The Stam building is remarkably elaborate for a town of about 2400 people, with its varied brickwork, white painted metal cornices, sandstone details and multi-level Mansard roofs. The doorway and window treatments at ground level no longer adhere to the original design but the building is well maintained.

15.A low-pitched hip roof on this two-storey wooden commercial building built by the Spencers reminds one of #10 across the street. Long neglected, this prize example of a retail establishment, which must date to some time prior to 1877, has been beautifully painted and its cornice and brackets restored. The projecting display windows are among a very few originals that still survive in the town.

16.This impressive bank was carried out in a neoclassic style, so popular from the 1820's onwards, expressing timeless strength in architecture. Built in 1929, amid some furore because It replaced a large 18th-century brick building at this location, the result is quite successful and untouched by later modernization. The entire facade is of sandstone and suggests a temple front in the Ionic order. The inset carvings of swags mid-way up this monumental facade reveal that the architect was softening the effect a little by introducing a device popular with French neo-classicists.


17.A restoration program of major proportions was accomplished with private funds in the late 1970's when the old tavern building, called the White Swan, reemerged after generations of abuse and neglect. An archaeological excavation img/pic17.JPG (17853 bytes)yielded some 70,000 objects from around the site, and the beauty of the Flemish bond brickwork with glazed headers was brought back to life. Having been built by Joseph Nicholson about the middle of the 18th century, this rare surviving tavern is said to have provided refreshment to George Washington himself on one of his visits to the Town. Michael Bourne, the restoration consultant, removed some later dormers, corrected the design of the full-width porch and moved back the old kitchen building at the rear.

In another phase of the plan to convert the White Swan into an inn, the building next door at High Street, an 1895 drug store, was also restored to its proper appearance at ground level while the second-storey space was linked to the White Swan to form a large "Victorian" suite.

18.Cross Street south to the railroad tracks has been largely a commercial area for a very long period. This is one of the shops whose occupants changed with some frequency and has been in existence for perhaps a century. A recent partial restoration revealed many internal changes and the covering up of a curious set of second-storey "jib doors" above the display windows. Now presenting an attractive appearance, this property was the subject of a legal suit between the former owners and the Town. The Historic District Commission had insisted that all modifications to the structure be applied for. In supporting the correctness of the Commission's position, the Maryland Court of Appeals in 1981 upheld the wording of the Town's Ordinance as intelligible to the layman and pointed out the Commission's right to consider the effect that a building may have upon the general "streetscape". This Chestertown case has drawn national attention and encouraged preservation commissions elsewhere.

19.Constructed between 1908 and 1909, this was the Town's first sizeable volunteer firehouse. By the 1890's there was talk of upgrading the primitive engine house located near the market building on High Street. The style chosen was a severely geometrical one. The bell tower, subsequently removed, hasrecently been put back during a fine job of adaptive reuse of the building carried out by Annapolis architect, James W. Burch. Ironically, the firehouse was no sooner built than Chestertown suffered its worst general fire. The entire commercial block on the other side of Cross Street was destroyed in 1910.

20.The railroad began to play an important role in the economy of the town in 1872, the line extending all the way down to the Chester River wharves. This surviving passenger station, which has been moved from the foot of Cross Street to allow for improvement of the thoroughfare, still provides a charming reminder of days gone by. Built ca. 1905 in a popular timber and stucco style that is admirably suited for the provision of wide sheltering eaves, the station is one of the few of this style remaining on the Delmarva Peninsula.

21. Originally built as a church in 1859, this edifice has spent most of its life in secular uses. The Methodist Protestants of Chestertown broke away from the main body of the church by 1830 and at first used a very simple building. Their new brick, temple-like structure of 1859 had, when still a church, tall windows along the flanks and a sanctuary (still visible) at the rear. After the congregation moved to High Street some thirty years later, the building became part of the adjacent public school buildings; and, finally, since around the turn of the century it has housed various printing operations. Although the flat vertical pilasters and the cornice around the building hint at the fading Greek Revival style, the heavy bracketing under the roof points to the later mid-century period.

22.The cornerstone for Janes M. E. Church had only just been laid in 1914 when the twin-towered, Gothic style 1860's building belonging to the congregation on South Queen Street went up in flames. The church is named after Bishop Edmund S. Janes in response to his appreciation of this black congregation's work in Chestertown. This building, constructed of hand-made bricks, represents also the congregation's continued appreciation of the Gothic style - the style still visible at this date in both Christ Methodist and First Methodist over on High Street. The church has a well finished interior and remains virtually unchanged.

23.This nicely proportioned three-storey building is one of a number needed to replace the losses that this commercial block suffered in the great 1910 fire. its tidy brick-faced facade seems to combine two style trends of the 'teens and 'twenties: the "Prairie" and Renaissance-revival styles. The simple band of rectilinear windows at top and the wide frame rectangle of the ground storey fit the "Prairie", while the subdivided arched window of the middle storey is in the Renaissance mode. The short tile roof over the entrance is a later addition.

24.The detailing of the roof zone in this delightful structure suggests that the builder had in mind that the facade would face all those approaching the business district via Spring Avenue. Its eye-catching steeple, triangular windows, stained glass, fish-scale shingles, etc., all fit the exuberance of the late 19th-century Queen Anne style. Below the cornice line, however, the building has been refaced; and a Colonial Revival frame, complete with broken pediment, surrounds the display window and doorway. This building must have been at the outer edge of the 1910 conflagration.

25.This frame house represents in reduced scale the Italianate style of residence, as seen at #2. It was constructed by local carpenter William D. Smith and shows the familiar bracketed cornice (with corner pendants), heavy hoods above the windows, and a full-width porch that has unfortunately lost some of its detailing. The house once had an outdoor kitchen at the rear of its larger back addition. The paint scheme has now been restored to one popular in the mid-19th century at the time the house was built.

26.This is the only remaining so-called "telescope" house in town. This type of additive construction can even be found in some of the grander residences of the Eastern Shore. The late eighteenth-century part is a storey-and-a-half, has beaded clapboarding and some of its original panes of glass. The taller section was added some time in the nineteenth-century before 1877 and shared the large chimney that was on one end of the middle section. Here a change in type of clapboarding, dormers and other details can be discerned.

27.A charming, small-scale tradesman's house, nicely restored and datable to 1771-1783. Its two end-chimneys are sheathed in clapboard except at the bottom. Added living space was achieved with two rear additions to this building, which has been facetiously referred to as Sterling's Castle.

28.Something of an isolated survivor in this street, this five-bay brick house has a history going back to the second quarter of the 18th century when it seems to have been built by a member of the Ringgold family. The structure has undergone a slow but worthwhile restoration and one can see around to the side an early lean-to addition, known locally as a "catslide" roof.

29.Despite the wide based appeal of the Gothic Revival style in America from the 1830's onwards, very few examples can be found today in the Historic District. Fittingly, the finest is an excellent church, designed by Baltimore architect Benjamin Buck Owens in 1887, and constructed at a cost of about $29,000. The prospering Methodist Protestant congregation moved here from its Cross Street building in the following year to enjoy one of the most richly ornamented buildings ever constructed in the Town. The irregular composition is dominated by a multi-staged tower with pointed steeple, placed midway against the building. A lower polygonal turret is close to the street on the other side of the edifice. Gothic arches, stained glass and buttresses are found all around. The textures of brick, stone and slate are well handled in a building which might also be called "High Victorian". Strangely, the rear section of Christ Methodist, now visible, was long hidden from view by a preexisting adjacent building at the corner of Mill Street.

30.The tall bay window and gable-end of this residence echo some of the features of the nearly contemporary church alongside. A long L-shaped porch fits well into the deep narrow lot. Now in a good state of repair, the Historic District Commission played a role in saving this building, much to the satisfaction of all involved.

31. This is one of a few surviving large-scale houses remaining on this side of High Street just above the Market Space. Built in 1877 in a rather conservative style for Thomas Hubbard, the facade is in five parts and absolutely symmetrical; and much of the detail, like the bracketed eaves and hooded windows had been in use for some decades. The ironwork atop the hip roof and the Eastlake style decoration of the porch columns give it an up-to-date appearance. Doubtless a more varied color scheme once set off this solid house.

32.This building was erected in 1901 as the public school and is a prime, early example of Colonial Revival in one of the Town's public buildings. The mass of the structure is emphasized by the entrance tower, a high gambrel roof, and a pair of large dormer windows (likewise gambrel roofed). The tower originally had two more stages; a balustrade, surmounted by an open cupola. Typical of early Colonial Revival is the use to excess of motifs like the Palladian window (in the tower and two dormers), expensive Flemish bond, and stone trim. on this site once stood one of the most imposing mansions of the Town, United States Senator George Vickers' three-storey Italianate residence that faced Mill Street.


33.The cornerstone of the present U.S. Post Office was laid in 1935 after the removal of a large, but nondescript old commercial hotel. The new structure, designed by the Baltimore firm of Lucius White and Henry Perring, is a striking example of Federal Revival architecture. Bearing a resemblance to such a mansion as "Homewood" (1803) still in Baltimore, the Post Office features a tall single-storey effect, with inset panels in the wall above the windows, and, above all, an elegant portico of slender columns with exquisite detailing above the doorway. Buildings of this elegance were not financially feasible in early 19th-century Chestertown. The local post office had had many locations, the last being Stam's Hall, before this building was erected.

34.This Methodist meeting house was put up between 1801-03 after a commission of the State Legislature granted the congregation a small portion of the western end of the Market Space. The brick structure resembles, in somewhat simplified form, the appearance of the earlier Emmanuel Protestant Episcopal church situated to the east of the market Space; and the two are topographically aligned. There was originally a single main door, facing High Street, and another smaller one on Club Lane (now Spring Avenue). It Is in Flemish bond brick and its original main doorway seems to have been more understated than the present one. The first American Methodist Bishop, Francis Asbury, preached here and the success of Methodism was such that other congregations arose in Town and this building became inadequate for the main group. It was abandoned to a variety of public and commercial purposes when the new house of worship was built further up on the same side of High Street in 1877,

35.Probably built by William Slubey, local merchant, in the late 18th or early 19th century, this building is the oldest along Park Row, facing the old Market Space. Beneath later coverings and modifications one can visualize one of the few remaining five-bay, 2 1/2-storey clapboard dwellings in town. Two lots to the rear off Spring Avenue, there stands an original, early, small brick smoke-house, belonging to another property.

36.The old tavern and restaurant, known as the Rockwell House (probably after the mid-nineteenth century owner) appears today to be a building of the immediate pre-Civil War era. Its narrow block-like form carries a low metal roof, clapboard siding (beneath the asbestos), and modest corner and window treatments, details that indicate the lingering popularity of Italianate design.

37.Emmanuel Church is almost literally the physical cornerstone of the Chestertown plan, and it is in this building that an important new spiritual cornerstone was laid. In 1780 a small group of Anglican clergymen met in the 8-year-old building to coin a new title which would signify the break with England: The Protestant Episcopal Church. That term has, of course, been in use ever since. The structure has undergone much modification from its original 2-storey, 5-bay format. The building was entered on the long side facing High Street and above the door was a costly Palladian window. The wall was in all-header bond. The Georgian effects were changed in the 1880's when the sanctuary was moved to the southeast (short) end, and the entrance shifted to the northwest end opposite. The pitch of the roof was changed, in keeping with a more medieval look; and the windows of the former entrance wall became single tall openings filled with stained glass. An entrance tower and parish hall improvements were effected in 1905. Among the many famous rectors of this church was Dr. William Smith, former Provost of the College of Philadelphia and founder of Washington College. of the most important acts in establishing a port of Chestertown in 1706 was the provision for a court house. The earliest known plat of the town shows the 18th-century, apsidal-ended court house in the center of a large area of public ground with Emmanuel Church in one corner and the cemetery or church yard using much of the rest. A small jail stood behind the court house, the latter being of about the same size as the church in the late eighteenth century. The front section of the present court house was built in 1860, using a T-shaped plan whose main axis faces High Street. This, the oldest surviving part, is in essentially Italianate style, solidly built of hard, dark brick, with typically low roof, wide eaves, and elongated brackets along the cornice and on the doorframe. With the cemetery gone and the need for interior space pressing, a Colonial Revival addition was attached to the rear, with access from Cross Street, in 1969.

39.In 1826 the Maryland General Assembly granted this small lot on the public land to the Masons and by 1835 the Masonic temple is referred to in a deed. The construction was of a very simple and consistent sort, resembling the two churches already on this axis, with the exception of the wide cross gable that breaks into the roof line above the main entrance. Undoubtedly, this once contained a circular window that has since been blocked off. The Masons had a fine hall on the second Storey, but as early as 1849 this was abandoned to a newspaper establishment. The structure was known for decades as the Kent News building while many other offices and enterprises operated on the ground Storey. A one-storey clapboard addition was put on, perhaps as early as 1877, to accommodate the demand for this central location.

40.Nineteenth-century accounts refer to lawyers' offices in the area of the Market Space and all around the Court House, but by mid-century there was a movement to create a series of small street-side offices along Court Street for legal practitioners. Chestertown's Lawyer's Row is an excellent example of this tendency in small-town county seats. The street is quiet and tree-shaded, and several examples, such as this, are in beautiful condition. This office, like its next-door neighbor at No. 115, was built in the third quarter of the century. Its tall entrance wall suggests a dignified chamber for consultation within. The hooded windows and the ornate pendant-brackets imply a certain restrained richness of taste, especially as compared with the more sparsely decorated cornice and doorway of the slightly earlier office at No. 115.

41.Like #40, this office is entered at the right. From the fact that it first appears on an 1885 map, we may gather that it was only recently built. Perhaps the most satisfying example of its type, one finds here a severe, dark, hard brick with thin tinted mortar joints, a formalizing pilaster effect at the two corners, and nicely related wood and tilted-brick friezes completing the top of the composition. The original dark door completes the authentic feeling of this office facade.

42.This small building was one of a few such on the north side of Church Street, or Alley, at the end of the 19th century. It has been neatly restored at ground level to its former appearance as a small shop (though it is now an office). A "catslide" roof can be seen around to the rear.

43.This impressive 31/2-storey 18th-century brick building comes as a surprise in its cramped location on little Church Alley. In fact, the plot of land around the house was entirely open between Court and Queen Streets down to the late 19th century, and the 18th-century court house faced this street. It is assumed that a bricklayer, James Moore, began the work in the second quarter of the 18th century after acquiring the land. But the main portion of this tall, solidly built townhouse seems to have been erected under the ownership of James Piper in the 1780's when full three-storey elevations were common in Atlantic coastal towns. The present form of the house with its rear wing resembles in some respects the Powel House in Philadelphia. All four corners of the structure are framed with unusual brick pilasters that taper at the top under the two heavy cornices which cap the front and back of the house. The tall double chimneys must have been especially impressive when the Queen Street side was open to view. Because Collector of Customs William Geddes (see #1) once lived here, the building is known as the Geddes Piper House. It is the headquarters of the Historical Society of Kent County, which bought and restored the property, using Henry Powell Hopkins, architect, to design the rather heavy Tuscan pedimented doorway.

44.This block of Queen Street features a great variety of smaller but comfortable residences, some of considerable antiquity. This frame house presents a mirror image of #46, for both were constructed by William Vannort ca. 1877 on small lots alongside #45. These houses retain their ground-storey front porches, which have now been stripped away from so many other houses of the era. The facades are nicely framed by slender pilasters and bracketed cornices, and the detailingaround windows and doorway reflects the continued popularity of Italianate design.

45.This small brick house may be the oldest on the street, the construction for the Buck family probably dating ca. 1735-1750. It is of Flemish bond, has a belt course between floors, and is notable for the irregular arrangement of window and door openings. The rear section of the roof slopes less abruptly, giving the "catslide" effect found in other early houses where additional space was added at the back.46.See the description for #44.

47.This common bond brick residence was built on the front of a ca. 1740 smaller house, whose original kitchen still remains in the basement. Local attorney Benjamin Chambers had the home built for his more famous son, Senator Chambers (see #65), in the 1780's. The construction resulted in a high front basement and taller lines for this three-bay, 2 ½ -storey structure. The building served as the rectory for Emmanuel Church during the later 19th century.

48.Of similar size and three-bay construction to #47, this house has the distinction of being associated with the Nicholson family, prominent in the Navy during the Revolutionary War period. The owner, John, served on several vessels and was ultimately Commander of the Continental sloop Hornet. Brother James was head of the Maryland Navy and then head of the Continental Navy from October 1776 until 1785. A third brother, Samuel, held several commands culminating in the 1790's when he not only commanded the U.S. Navy's Constitution but supervised its construction.This 1780's house has architrave blocks over the windows and a brick dentil cornice. It was expanded by 1885 to include a dining and kitchen wing at the left, and the doorway detail seems to date from that epoch.

49.This 1770's brick house was extensively modified at the beginning of this century. A thorough restoration has removed most of the accretions, such as the lengthy verandah, porte-cochere, etc. The essentially simple house, built for Dr. William Houston in Flemish bond, has thus reemerged. The dormers are of a later time, however, and the brickwork at the left front suggests that the house was enlarged from three to five bays at an early date.

50.Severely abused in our century, the John Greenwood house of ca. 1867 represents yet another example of the long-lived popularity of simplified Italianate design in Chestertown. The house had a wing at the rear-left by 1877; and when Preservation, Inc., decided at great cost to rehabilitate this house, which had been all but gutted by fire, the decision was made to attach a modern rear wing at the same point. The fabric of the main block is essentially new but recreates charmingly the original effect. A small balustrade above the roof and a colorful paint scheme dress up this clapboard residence.

51. This commodious house was erected by A. M. and W. S. Culp in 1896 at a cost of $3,800. It was the second parsonage for Christ Methodist Protestant Church to be put on this site and contains elements, like the polygonal turret above the entrance, and the stained glass, which remind us of the church. This is, however, a very subdued late 19th-century version of Gothic. The color scheme is now appropriate to the turn-of-the-century era.


52.The capable and active local builder, Horace M. Stuart, constructed this modestly priced frame house around 1880. It presents to the passerby on Maple Avenue a wonderfully decorative, cut-out verge board under the eaves of the roof. This Gothic-inspired detail was picked up in the front porch decoration (now lost), the bay window, and the familiar bracketed cornice. The tall proportions of the house suggest grandness for the size of the lot and are likewise inspired by the Gothic trend.

53.Built by William Burchinal, member of a prominent merchant family, this is a larger and approximately contemporary version of #50. Even though on an exposed corner, it is only the facade that is kept in strict five-bay symmetry. The windows are hooded. The main door and window above have narrow sidelights. Now housing apartments, this Italianate building doubtless had a form of lantern atop the roof and was clapboard sided.

54.This pleasant late l9th-century residence, like its next-door neighbor at 107 Maple Avenue, was designed to take full advantage of the lot's width at a time when traffic was beginning to increase. The one-storey front porch runs parallel to the road and is set back, protectively, from the gabled bay-window wing of the house. The occupants thus enjoyed a good view, both indoors and outdoors, of the passerby. The asymmetrical plan also allowed for a maximum amount of decoration on the street front.

55.Built for judge James Pearce, son of United States Senator Pearce (see #3) in the mid-1880's with the help of the capable Chestertown contractor H. M. Stuart, this house is one of the most striking in Town. Educated at Princeton, Pearce and his wife had undoubtedly seen some of the more extreme designs around the New York-Philadelphia area in the Queen Anne style. There is here an extreme picturesqueness of effect in the L-shaped plan (just the opposite of #53). The roof is irregular and holds dormers of different shapes; the walls move in and out, supporting open porches and closed, shallow projecting bay windows. Above all, there is a dramatic variety of colors and textures: brick, timber, clapboard, wood shingle, stone, stucco, slate and terra cotta. The house is a tour-de-force (costing $8,000!) which one could not miss on reaching Town from the south. After leaving the Pearce family, the house served for a time as the Emmanuel Church rectory. In recent years it has been carefully restored.

56.In 1805 a corporation built a wooden bridge across the Chester River at the foot of Maple Avenue (then Fish Street). This development added great importance to this comfortable three-bay brick house, which had been first constructed in the mid-18th century. In its present form, one can see additions to the left and rear; and although a 19th-century porch that once surrounded the entire ground storey has disappeared, the lowered, bracketed roof remains, as does the later main doorway. There once stood at the edge of this important property the small toll house which collected tolls until the bridge was made free in 1890 by the two counties.

pic57.jpg (2766 bytes) 57.Dating from around World War 1, this substantial house stresses the virtues of solidity, dignity and restraint. Made of hard, dark brick with thin mortar and slate roofing, the essential lines are severe, while retaining such late 19thcentury amenities as a solidly built, full-width, large front porch, a two-storey bay window, and the formal porte-cochere (at left rear).
pic58.jpg (3304 bytes)58.An interesting thing about this early brick residence is that it was for generations the only dwelling on the town side of this Water Street block. Much of the adjacent land between Maple Avenue and High Street had been reserved by the waterfront houses for gardens and auxiliary uses. The house was probably built for the Frisby family around 1766 with a simple three-part facade. The front wall is in all-header bond while the ends are in common bond. Only the south wall had windows on two floors; the north wall windows and the porch are later changes.

59.Built in the third quarter of the 18th century, perhaps for Simon Wickes, this house resembles #58 in most respects. It likewise has an all-header bond brick front, but the water table jogs above the basement windows and the north wall is in a fine Flemish bond with glazed headers. The restoration of the building includes a small porch with benches, such as are known to have existed in 18th century Chestertown.

60.This waterfront double residence is actually a late 19th century building to which additions have been made. It harmonizes with other residences in this block because of the Colonial-Revival entrance porches and the simulated stone architraves above the facade windows. The scroll brackets at the ends of the roof cornice are clearly from the period of first construction, however.

61.Known as the Watkins house because Esau Watkins received the land as a wedding gift in 1739 from his Ringgold in-laws, this may be the oldest house surviving on Water Street. it is hip-roofed with a coved cornice and is oriented perpendicularly to the street. The walls are chiefly of Flemish bond with glazed headers but a simpler section was added to the river front. Much of the detailing is restored.

62.Now known as River House, this National Register landmark was first owned by Thomas Smythe, merchant and shipbuilder, and then Peregrine Letherbury, attorney, during the 1780's. Law professor Peregrine Letherbury was first secretary and later President of the Washington College Board of Visitors and Governors. Letherbury is thought to have completed this very elegant mansion, perhaps the finest of the immediate post-Revolutionary period in Chestertown. Tremendous attention was paid to the high three-storey facade, which rises above a tall basement. The Flemish bond street wall is framed by slender brick pilasters at the sides, a cut stone water table, and an extremely fine cornice under the low pitched roof. The two main floors are separated by a simple stone belt course and their windows topped with rusticated stone flat arches. The moldings of the cornice are especially refined (egg and dart, dentil, etc.) and serve to tie in the pilaster capitals. The superimposed porches of the river front and the entrance doorway are the work of Orin Bullock, nationally known restoration architect. The building is currently privately owned and paneling from a second floor parlor is now in the Winterthur Museum.

63.The Richard Hynson house of ca. 1870 originally consisted of a three-storey main block, two bays deep. The style is in the familiar, by now quite conservative, Italianate, as can be seen from the hooded first- and second-storey windows, the tripartite treatment of the main door and the window directly above, as well as the low-pitched, heavy bracketed roof. Mr. Hynson had a lower rear wing already by 1877, if not before, and this was further added to by 1885. Today the structure is greatly enlarged to form an apartment building.

64.Perhaps the most radically transformed early house in Town, the Thomas Anderson residence of ca. 1796 seems to have been five bays and 21/2 storeys at first and then modified to suit the Italianate style at mid-century when the third floor, bracketed cornices, hooded windows and front porch were added. A service wing was in place at the north end by the later century, certainly, and a marvelous two-storey oriel window of the Queen Anne type was put on at the south end. Today, its lengthy and irregular facade is one of the most interesting in this impressive section of the waterfront "streetscape".

65.Widehall is in many respects the Town's most satisfying mansion. Built by Thomas Smythe, merchant and shipbuilder and perhaps the wealthiest man in Kent County, in this pivotal location ca. 1770, the house is commodious and quietly formal. The facade entrance portal is not placed within an impressive central projecting "pavilion" with a wide pediment along the roof line, as in most mansions of this era (Hammond-Harwood house in Annapolis or Mount Pleasant in Philadelphia) but its five-bay facade remains flat, as in the Corbit-Sharp house in Odessa, Delaware. The quality of the building depends on its fine proportions and well executed details, such as the high stone foundation, the beauty of its half-columned Doric portal, and the fine frames around the 12 over 12 windows, which are capped by keystoned flat arches.The house takes its name from the large space allotted for the hall and staircase on the street side of the house (reminiscent of Mount Pleasant). The dormered hip roof was restored shortly after 1905 when Mr. and Mrs. W. W. Hubbard acquired the much-altered house. The tall Ionic porch on the river front is also of this later era, but to Mrs. Hubbard belongs the credit of being the first leader of historic restoration in Chestertown. One of the appreciative early residents of this gracious home was United States Senator Ezekiel Chambers, later judge and President of Washington College's Board of Visitors and Governors.


First Methodist Church

The First Methodist Church on High Street, corner of Mill, today appears as a handsome Colonial church in a beautifully maintained state. In actual fact, the structure was built in 1877 at a cost of about $20,000 in a symmetrical Gothic style, complete with medieval-looking steeple. During the 1920's this prosperous congregation wanted to enlarge the church complex and do over the main building in the increasingly fashionable Colonial Revival style. A new Ionic portico was erected in front of the old tower, which was itself done over in the Georgian idiom. Most of the original church has been masked out by alterations, but a careful study of the lower side walls reveals the vestiges of the old Gothic buttressed wall. First Methodist Church presents the case of a well-intentioned improvement of a building. Handsome though the result may be, a part of the past has been lost.

Palmer "Rock of Ages" (532 High Street) This modest 1 ½ -storey dwelling at the upper end of High Street has long been thought to be one of the oldest in Town (mid-18th century). It is the only early structure of solid stone, certainly, and appears in a very old photograph with a one-room addition at the northwest end. The present front porch is less than a century old.

Colin Stam House (114 Washington Avenue) The house of entrepreneur Colin F. Stam at the foot of Washington Avenue marks an important transition in the life of the Town, namely the development of an impressive row of residences on the main road leading out to Washington College. Stam's house was built in 1877 for about $4,000 (in the main section) by local builder H. M. Stuart. It is an eclectic design which mixes Gothic elements with some Second Empire characteristics that were to be used in more florid fashion in Stam's Hall of 1886. The masonry work in the chimneys is especially well done.

125, 127, and 129 Washington Avenue These three comfortable homes illustrate the rapid growth of Washington Avenue in the late 19th century when the College began to open its lands on a 99 year lease basis. All three wooden buildings feature large gables facing the street with the rest of the house massed alongside, two with stout towers. Extensive verandahs with intricate detailing still surround these buildings, adding to the feeling of spaciousness. Their style may be referred to nowadays as Queen Anne, a rather loose term. In their day they must have seemed to their occupants a wonderful escape to the outlying countryside. No. 125 has some especially fanciful decorative trim surviving. Color schemes for such houses were never all white, however.

Bungalow at 311 Washington Avenue This delightful dwelling marked the first arrival in Town of a Sears & Roebuck prefabricated bungalow. This class of house had great vogue in California, and the present example, which features a low, wide, tiled roof, is in the "Craftsman" style. It arrived in Town by rail in 1926.


Between 1845 and 1854, three rectangular-shaped buildings were erected on the brow of a hill, facing town, to comprise the new Washington College campus. They were erected precisely over the site of the College's first building which was destroyed by fire in 1827. The earlier building, constructed under the leadership of Dr. William Smith and with the support of General George Washington, had been begun in 1784. Excavations at the site in 1981 proved that the building had measured 160 feet across the main front, making it one of the largest 18th century Georgian buildings in Maryland and one of the largest College edifices in the new nation.The new center building, Middle Hall, was used for classrooms and dormitory. There are vestiges of the Greek Revival in its broad banded exterior cornice, but the porch details and the roof lantern (reconstructed) are in the more up-to date Italianate mode. East and West Halls, built slightly later, are simpler and have more vertical proportions. All three buildings are of hard, dark brick with thin mortar joints and have low metal roofs, common in the mid-century (see #36). Washington College is Maryland's oldest institution of higher learning and the three buildings are on the National Register of Historic Places.


In 1732, a generation after the founding of Chestertown at its present site, the Maryland Assembly passed a law, requiring that all sheep, geese and swine be kept penned up in town because of the nuisance and danger they caused. In 1963, the Maryland legislature passed another protective law for the common good - one already approved in several other American states and in many European countries - a piece of legislation allowing local governments in the State to watch over their architectural heritage.The Town of Chestertown was quick to recognize the value of this enabling legislation (Maryland Annotated Code, Art. 66B) by adopting an ordinance in the very next year, giving full powers to a locally appointed seven-member commission. This group now meets in formal public sessions the first Wednesday of every month to consider applications for work to be done within the "Historic District," as defined by the ordinance. The work in question is exterior work that will be visible from the "public way."The following are examples of the sort which require a permit: signs; auxiliary structures, such as sheds and fences; additions to a main structure, such as porches, wings, dormers, chimneys, shutters, railings, or the removal thereof; replacement or recovering of the sides or roofing of a building, whether in part or entirety; painting masonry surfaces; the construction of entirely new buildings or the demolition of existing buildings. The Town Office is in a position to advise the public further as to what work falls within the requirements of the law.The seven Commissioners are civic volunteers who give of their time and experience and who are more than happy to assist their fellow citizens in making appropriate decisions which will both meet owners' needs and at the same time fit the criterion of architectural propriety. Purely conceptual approvals cannot be given, however.The fairness and correctness of the Chestertown Commission's proceedings have been substantiated in some important higher court rulings (which have attracted national attention) and, more recently, in the National Park Service recognition of Chestertown as a Certified Local Government (the fourth in Maryland to be so approved). Chestertown has a National Landmark District, and that district was listed with the National Register of Historic Places in 1968. The National Register District was further expanded in 1984, Additionally, the Chestertown government now has the authority to nominate individual buildings to the National Register.


This guide was produced by the Mayor and Council of Chestertown, using matching grant funds received from the National Park Service, United States Department of the Interior. These Federal funds were administered by the Maryland Historical Trust through the Certified Local Government Program.

The text of this guide was written by Robert J. H. Janson-La Paime. Assisting in research was Kathleen B. White. The Project Coordinator was William S. Ingersoll.

The Historical Society of Kent County, Maryland

The Historical Society of Kent County, Maryland, is a non-profit organization dedicated to the collection and preservation of artifacts, documents, and information that aid in the interpretation of all aspects of Kent County's history. The Society shares this information through its research library, museum space, programs, publications and website in order to foster a knowledge and understanding of the shared heritage of the community. The Society supports and encourages the preservation of historic buildings and sites throughout Kent County.

Click here to visit the Historical Society website.

Chestertown Self-Guided Tours

African American History Tour
Audio-Guided Tour of the Chestertown Waterfront