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May 11 – RiverArts Salon: This Year's National Music Festival with Richard Rosenberg and Caitlin Patton

Arts Alive! - online

This summer, the National Music Festival celebrates its 10th Anniversary in Chestertown. Learn how NMF has flourished over its first decade, and about plans for this year’s Festival Aug. 1 – 14. From symphony concerts to a little Gershwin to kid-friendly activities, get the low down from Artistic Director Richard Rosenberg and Executive Director Caitlin… Continue Reading May 11 – RiverArts Salon: This Year's National Music Festival with Richard Rosenberg and Caitlin Patton

Merlot Vertical Tasting & Pairing

Crow Vineyard & Winery - 12441 Vansants Corner Road, Kennedyville, MD 21645

Join us for a vertical tasting of Merlot: 2015 Merlot, 2016 Merlot and 2019 Merlot Reserve. Crow winemaker, Michael Zollo, and local wine enthusiast Jon Peterson will walk you through tasting each wine, talk all things merlot, how it’s made and how it pairs with small plates of Crow tidbits. Opportunity to purchase limited release… Continue Reading Merlot Vertical Tasting & Pairing

Bohemia Wood Fired Pizza & Wine

Crow Vineyard & Winery - 12441 Vansants Corner Road, Kennedyville, MD 21645 - Crow Vineyard & Winery - 12441 Vansants Corner Road, Kennedyville, MD 21645

Join us for a glass of award-winning Crow wine and a personal wood-fired pan pizza by Chef Paul McCormick. Ticket includes 1 glass of featured Crow wine, 1 personal pan pizza and a salad. Additional food and wine by glass or bottle will be available for purchase.

Wine & Yoga Happy Hour

Crow Vineyard & Winery - 12441 Vansants Corner Road, Kennedyville, MD 21645

Join us for our 2nd Wine & Yoga Happy Hour taking place in May! Enjoy a 1-hour yoga session, taught by Alyson of Serenity Yoga, while overlooking the vineyard. Afterwards sip and snack on Crow wine and a cheese pack. Additional food and wine will be available for purchase. Ticket comes with 1 glass of… Continue Reading Wine & Yoga Happy Hour

Chestertown Farmers Market

Fountain Park

UPDATE 3/23/2021 - The full season of the Chestertown Farmers and Artisans Market opens Saturday, March 27 and will continue to the week leading up to Christmas. Artisans, who are back after the winter pause, and new and returning farm vendors will be set up from 8 a.m. to noon every Saturday in the 200… Continue Reading Chestertown Farmers Market

SUSPENDED – Saturday Mornings at KidSPOT!

KidSPOT at RiverArts Gallery 315 High Street Suite 104, Chestertown

We’re busy at KidSPOT distributing craft bags to help kids in less affluent parts of our community have access to art materials and projects until we can open again. If you’re interested in supporting this initiative, please visit our website at https://chestertownriverarts.org/kidspot/ and make a donation. Thank you!

MassoniArt presents Finding Light.1

MassoniArt - 203 High Street - MassoniArt - 203 High Street

Featuring Greg Mort, Katherine Cox, Claire McArdle, Grace Mitchell, Heidi Fowler, Zemma Mastin White, Catherine Kernan, Elizabeth Casqueiro, Kathryn O’Grady, Kenneth Schiano, Eve Stockton, Carol Rowan, Jon Mort, Simma Liebman, Blake Conroy, Shelley Robzen, Vicco von Voss Although we have increased to 10 the number of guests visiting the gallery, we are still requiring masks,… Continue Reading MassoniArt presents Finding Light.1

Bohemia Wood Fired Pizza & Wine

Crow Vineyard & Winery - 12441 Vansants Corner Road, Kennedyville, MD 21645

Join us for a glass of award-winning Crow wine and a personal wood-fired pan pizza by Chef Paul McCormick. Ticket includes 1 glass of featured Crow wine, 1 personal pan pizza and a salad. Additional food and wine by glass or bottle will be available for purchase.

Justice Day: In Pursuit of Racial Equity in Chestertown, Maryland

Chestertown

Saturday, May 15 at 3:00 - 4:45 pm ET via Zoom Justice Day: In Pursuit of Racial Equity in Chestertown, Maryland Please join the James Taylor Justice Coalition of Sumner Hall to listen and/reflect upon the collective voices of those that lived in what came to be called Chestertown and of how justice-equality was a… Continue Reading Justice Day: In Pursuit of Racial Equity in Chestertown, Maryland

Bohemia Wood Fired Pizza & Wine

Crow Vineyard & Winery - 12441 Vansants Corner Road, Kennedyville, MD 21645

Join us for a glass of award-winning Crow wine and a personal wood-fired pan pizza by Chef Paul McCormick. Ticket includes 1 glass of featured Crow wine, 1 personal pan pizza and a salad. Additional food and wine by glass or bottle will be available for purchase.

May 18 – RiverArts Salon: Artists & Social Change: An Online Tour of the Smithsonian American Art Museum

Arts Alive! - online

This 90-minute salon will be longer than our usual session! Register to get the Zoom link provided by the Smithsonian, which is unique to this week (& different from our usual weekly Zoom). Join Bob Ferguson, a docent with the Smithsonian American Art Museum, for an online tour with the theme of Artists and Social… Continue Reading May 18 – RiverArts Salon: Artists & Social Change: An Online Tour of the Smithsonian American Art Museum

Merlot Vertical Tasting & Pairing

Crow Vineyard & Winery - 12441 Vansants Corner Road, Kennedyville, MD 21645

Join us for a vertical tasting of Merlot: 2015 Merlot, 2016 Merlot and 2019 Merlot Reserve. Crow winemaker, Michael Zollo, and local wine enthusiast Jon Peterson will walk you through tasting each wine, talk all things merlot, how it’s made and how it pairs with small plates of Crow tidbits. Opportunity to purchase limited release… Continue Reading Merlot Vertical Tasting & Pairing

Cars on High

Downtown Chestertown - 300 block of High Street, by Fountain Park

This series of gatherings takes place in downtown Chestertown every third Thursday of the month, April through October, from 6:00 to 8:00 p.m., weather permitting. The Town closes the 300 block of High Street, adjacent to Fountain Park, beginning at 5:30 p.m., and owners line up their antique, exotic, classic, or custom cars to share… Continue Reading Cars on High

Connect4Kent School Golf Tournament

Chester River Yacht & Country Club - 7738 Quaker Neck Road - Chester River Yacht & Country Club - 7738 Quaker Neck Road

On Friday, May 21st, Kent School will host the Connect4Kent School Golf Tournament at the Chester River Yacht & Country Club. We look forward to the first opportunity our community has to CONNECT in person during the 2020 - 2021 Academic Year. The School will work closely with CRYCC Staff to ensure that the tournament… Continue Reading Connect4Kent School Golf Tournament

Wine & Yoga Happy Hour

Crow Vineyard & Winery - 12441 Vansants Corner Road, Kennedyville, MD 21645

Join us for our 3rd Wine & Yoga Happy Hour taking place in May! Enjoy a 1-hour yoga session, taught by Alyson of Serenity Yoga, while overlooking the vineyard. Afterwards sip and snack on Crow wine and a cheese pack. Additional food and wine will be available for purchase. Ticket comes with 1 glass of… Continue Reading Wine & Yoga Happy Hour

RiverArts Salon: The Artistic Adventures of Blue Tulip with Posey Boicourt

Arts Alive! - online

A RiverArts Salon is a (virtual) place to learn something new, share ideas, explore interesting topics, see and be seen, and have fun. Based on her book Blue Tulip: an artistic adventure with painter Francois Joseph Kinsoen and his niece Adele, author Posey Boicourt invites you along as she rediscovers the world of a forgotten… Continue Reading RiverArts Salon: The Artistic Adventures of Blue Tulip with Posey Boicourt

May 26: Liberate the Landscape with Paul Santori

Arts Alive! - Tish Gallery (343 High St.)

Class will start at Tish Gallery (343 High St.) in downtown Chestertown. There, we will look at different ways artists portray landscapes (impressionist, pointillist, abstract, and traditional art in all mediums) to show examples and learn that it's fine to have your own style. Then, our group will move on to Fountain Park to draw… Continue Reading May 26: Liberate the Landscape with Paul Santori

FESTIVAL FORUM from the National Music Festival

Live Stream Virtual Event - Virtual Event - To register click: www.nationalmusic.us Chestertown

NMF celebrates its 10th Anniversary Festival, in Chestertown, Aug. 1–14. Leading up to the occasion, a series of delightful live discussions recalling the decade will be held via Zoom on 4th Thursdays, April - August. May 27, 7-8 PM, features Dana Goode, violinist, who began touring and performing at age 16 as a member of… Continue Reading FESTIVAL FORUM from the National Music Festival

Virtual Photo Club (Free!)

RiverArts Education Center - 200 High St

Undaunted by social isolation, RiverArts Photography Club facilitator Steve Kane hosted the first meeting of a new online version of the club on Thursday, March 26, using the Zoom platform. The club normally meets the fourth Thursday of each month at the ArtsAlive Education Center from 7 to 9 pm, and provides a forum for discussion… Continue Reading Virtual Photo Club (Free!)

Wine & Yoga Happy Hour

Crow Vineyard & Winery - 12441 Vansants Corner Road, Kennedyville, MD 21645

Join us for our final Wine & Yoga Happy Hour taking place in May! Enjoy a 1-hour yoga session, taught by Alyson of Serenity Yoga, while overlooking the vineyard. Afterwards sip and snack on Crow wine and a cheese pack. Additional food and wine will be available for purchase. Ticket comes with 1 glass of… Continue Reading Wine & Yoga Happy Hour

Ovation Dinner Theatre – Murder on the Menu

Crow Vineyard & Winery - 12441 Vansants Corner Road, Kennedyville, MD 21645

Join Ovation Theatre and Crow Vineyard as we present “Murder on the Menu”, an audience interactive production. The evening will include a three course dinner, the theatre experience and option to purchase bottles of wine at 10% off! Menu to come!

Cars on High

Downtown Chestertown - 300 block of High Street, by Fountain Park

This series of gatherings takes place in downtown Chestertown every third Thursday of the month, April through October, from 6:00 to 8:00 p.m., weather permitting. The Town closes the 300 block of High Street, adjacent to Fountain Park, beginning at 5:30 p.m., and owners line up their antique, exotic, classic, or custom cars to share… Continue Reading Cars on High

Juneteenth Celebration

Downtown Chestertown

More info coming soon! Juneteenth celebration: Friday June 18th, 2021 6-9pm Saturday June 19th, 2021 10am-8pm Sunday June 20th, 2021 11am-3pm  

Father's Day Bohemia Wood Fired Pizza & Wine

Crow Vineyard & Winery - 12441 Vansants Corner Road, Kennedyville, MD 21645

This Father's Day join us for a glass of award-winning Crow wine and a personal wood-fired pan pizza by Chef Paul McCormick. Ticket includes 1 glass of featured Crow wine, 1 personal pan pizza and a salad. Additional food and wine by glass or bottle will be available for purchase.

FESTIVAL FORUM from the National Music Festival

Live Stream Virtual Event - Virtual Event - To register click: www.nationalmusic.us Chestertown

NMF celebrates its 10th Anniversary Festival, in Chestertown, Aug. 1–14. Leading up to the occasion, a series of delightful live discussions recalling the decade will be held via Zoom on 4th Thursdays, April - August. June 24, 7-8 PM, features Jared Hauser, oboist, praised for his “subtle refined style” by Gramophone Magazine. He was appointed… Continue Reading FESTIVAL FORUM from the National Music Festival

Vines to Wine Farm to Table Summer Dinner

Crow Vineyard & Winery - 12441 Vansants Corner Road, Kennedyville, MD 21645

Join us for our 2021 Vines to Wine Farm to Table Summer Dinner! Start with welcome Sparkling and appetizers, then tour the vineyard to see our 2021 vine growth. You will then be seated on our patio for a 4-course meal crafted by celebrity Chef Robbie Jester and enjoy newly released Crow wines. Menu to… Continue Reading Vines to Wine Farm to Table Summer Dinner

Bay to Bay Bicycle Ride

Starts & Ends at Betterton Vol Fire Company

We want you to feel safe when participating in our bicycling event. Social distancing & precautions will be maintained. The Chestertown Lions Club welcomes cyclists to its summer bicycling challenge, the Bay to Bay ride. The tour consists of five routes between 26 and 102 miles in length. The flat loop routes take in the… Continue Reading Bay to Bay Bicycle Ride

Kent County Fair

Chestertown

The Kent County Fair is a traditional small county fair featuring great food, 4-H and community exhibits, animals, tractors, games and entertainment. The focus of the fair is agricultural education for the community and county youth. Each day features special entertainment and activities including 4-H auctions Saturday night. Each evening features a special dinner in… Continue Reading Kent County Fair

Cars on High

Downtown Chestertown - 300 block of High Street, by Fountain Park

This series of gatherings takes place in downtown Chestertown every third Thursday of the month, April through October, from 6:00 to 8:00 p.m., weather permitting. The Town closes the 300 block of High Street, adjacent to Fountain Park, beginning at 5:30 p.m., and owners line up their antique, exotic, classic, or custom cars to share… Continue Reading Cars on High

FESTIVAL FORUM from the National Music Festival

Live Stream Virtual Event - Virtual Event - To register click: www.nationalmusic.us Chestertown

NMF celebrates its 10th Anniversary Festival, in Chestertown, Aug. 1–14. Leading up to the occasion, a series of delightful live discussions recalling the decade will be held via Zoom on 4th Thursdays, April - August. July 22, 7-8 PM, featuresParker-Harley, associate professor of flute at the Univ. of South Carolina and an experienced orchestral soloist.… Continue Reading FESTIVAL FORUM from the National Music Festival

Run the Vineyards – Crow 5k

Crow Vineyard & Winery - 12441 Vansants Corner Road, Kennedyville, MD 21678

Run for Wine at the Amazing Crow Vineyard! NEW IN 2021 — Summer Evening Race featuring Post Race Barbecue!Race and Post Race Features Include: Chip-Timed 5K Run with instant results Flat Cross Country style course through the 365 acre farm and 12 acre vineyard Post Run Wine (1 complimentary glass of wine included for those… Continue Reading Run the Vineyards – Crow 5k

National Music Festival – 10th Anniversary Season

Various venues in Chestertown and Kent County

Come celebrate the 10th Anniversary season of the National Music Festival in Historic Chestertown on Maryland's Eastern Shore! From festival favorite, Brazilian guitarist Camilo Carrara, to symphony concerts. From Mozart and Mendelssohn to Gershwin and and Stravinsky — plus kid and family-friendly programing. Some concerts are free; others require a ticket. The festival brings together… Continue Reading National Music Festival – 10th Anniversary Season

Cars on High

Downtown Chestertown - 300 block of High Street, by Fountain Park

This series of gatherings takes place in downtown Chestertown every third Thursday of the month, April through October, from 6:00 to 8:00 p.m., weather permitting. The Town closes the 300 block of High Street, adjacent to Fountain Park, beginning at 5:30 p.m., and owners line up their antique, exotic, classic, or custom cars to share… Continue Reading Cars on High

FESTIVAL FORUM from the National Music Festival

Live Stream Virtual Event - Virtual Event - To register click: www.nationalmusic.us Chestertown

NMF celebrates its 10th Anniversary Festival, in Chestertown, Aug. 1–14. Leading up to the occasion, a series of delightful live discussions recalling the decade will be held via Zoom on 4th Thursdays, April - August. August 26, 7-8 PM, features Tom Parchman, principal clarinetist with the Portland Symphony Orchestra in Maine, and professor at the… Continue Reading FESTIVAL FORUM from the National Music Festival

25th Annual Chestertown Jazz Festival

Wilmer Park

Join us for 3 days of fabulous jazz featuring national and regional artists. The 25th Annual Festival begins Thursday, September 9 at the celebrated venue The Mainstay in Rock Hall.Wilmer Riverside Park will host the rest of the weekend's festivities. Opening Gala Cocktail Party & Concert on Friday evening. Saturday the afternoon of great jazz… Continue Reading 25th Annual Chestertown Jazz Festival

Cars on High

Downtown Chestertown - 300 block of High Street, by Fountain Park

This series of gatherings takes place in downtown Chestertown every third Thursday of the month, April through October, from 6:00 to 8:00 p.m., weather permitting. The Town closes the 300 block of High Street, adjacent to Fountain Park, beginning at 5:30 p.m., and owners line up their antique, exotic, classic, or custom cars to share… Continue Reading Cars on High

Cars on High

Downtown Chestertown - 300 block of High Street, by Fountain Park

This series of gatherings takes place in downtown Chestertown every third Thursday of the month, April through October, from 6:00 to 8:00 p.m., weather permitting. The Town closes the 300 block of High Street, adjacent to Fountain Park, beginning at 5:30 p.m., and owners line up their antique, exotic, classic, or custom cars to share… Continue Reading Cars on High

Dickens of a Christmas

Chestertown Historic District - 200 block High Street

Chestertown's Dickens-inspired holiday festival returns with more street performers, live music, food and drink, carriage rides, and more!

Holiday Market – Chestertown Farmers Market

300 block of High Street - Downtown by Fountain Park

Open Wednesday morning before Christmas. 8am-12pm Our bonus Pre-Christmas Farmers' Market will have both farm and artisan vendors.

TOWN GOVERNMENT MEETING SCHEDULE

  • Mayor & Council Meetings: 1st & 3rd Mondays, 7:30 p.m.
  • Utilities Commission Meetings: 1st Mondays, 7:30 p.m.
  • Planning Commission Meetings: 3rd Wednesdays, 7:30 p.m.
  • Historic District Commission Meetings: 1st Wednesdays, 5:00 p.m.

TOWN TRASH & RECYCLING SERVICES

The Town will be divided into two collection areas, both of which will be serviced twice each week. Collection of garbage and trash will be conducted in one area on Monday and Thursday evenings, and the other on Sunday and Wednesday evenings; except no collection will be made on New Years’ Day, Fourth of July, Labor Day, Thanksgiving Day or Christmas Day, but will be made on the next regular collection day after the holiday. Recycling: Paper, aluminum, household plastics picked up each Friday call 410-928-3333 (Infinity Recycling).

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