Plan your trip early and stay in Chestertown! Click here for local lodging.


MassoniArt presents Marc Castelli Annual Exhibit

MassoniArt – MassoniArt, 203 High Street

King’s Tide – Annual Exhibition October 25 – November 27, 2019 also featuring Chesapeake Boat Models by Ken Castelli Opening of the Exhibition & Reception Friday, October 25, 5-7:30pm Collector’s Preview – October 21-24 – by appointment November First Friday Celebration November 1, 5 -7:30 pm Marc Castelli – Gallery Talk Saturday, November 2 –… Continue Reading MassoniArt presents Marc Castelli Annual Exhibit

Annie: The Musical (Nov 22 – Dec 8)

The Garfield Center for the Arts at the Prince Theatre – 210 High Street

November 22 – December 8 Fridays & Saturdays at 7pm, Sundays at 2pm Directed by Jennifer Kafka Smith With equal measures of pluck and positivity, little orphan Annie charms everyone’s hearts despite a next-to-nothing start in 1930s New York City. She is determined to find the parents who abandoned her years ago on the doorstep… Continue Reading Annie: The Musical (Nov 22 – Dec 8)

MassoniArt presents Holiday Exhibition

MassoniArt – MassoniArt, 203 High Street

December 2019 – January 2020 Opening Reception – December First Friday – December 6, 5-7:30 pm New work by Gallery Artists and special guests. Featuring Susan Goldman, Carol Rowan, Kathryn O’Grady, Deborah T. Colter, Deborah Weiss, Zemma Mastin White, Kenneth Schiano, Celia Pearson, Blake Conroy, Nicole Fall, Heidi Fowler, Katherine Cox, Michael Kahn, James Tatum,… Continue Reading MassoniArt presents Holiday Exhibition

GCTV presents!

Garfield Center for the Arts 210 High Street, Chestertown

Watch a new LIVE performance each week on the Garfield Center for the Arts Facebook page – Don’t Facebook? Don’t worry! All content live streamed will be uploaded to our YouTube channel and shared on our website!

CANCELED – Chestertown HP Festival

Downtown – Chestertown

Terrible news friends! We have just received a proclamation from the minister’s office that all festivities scheduled for the 2020 Chestertown HP Festival Weekend have been hereby canceled! All wizards and wizarding friends are encouraged to subscribe to the Chestertown HP Festival mailing list to receive any notices as they become available. Fear not! The… Continue Reading CANCELED – Chestertown HP Festival

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 and make a donation. Thank you!


  • 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.


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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