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

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Recurring

Planning Commission Meeting

Town of Chestertown 118 N. Cross Street, Chestertown, MD

Any member of the public wanting to join the Zoom meeting should contact Kees de Mooy at 410-778-0500 or kees@chestertown.com CLICK FOR TOWN AGENDAS & MINUTES

Cars on High

300 High Street - Fountain Park

Come on out to Cars On High St. in Chestertown, MD to show off your Exotic, Classic or Vintage car on the 3rd Thursday of the month, April thru October.

Grape Stomp

Crow Vineyard & Winery - 12441 Vansants Corner Road

Join us in celebrating our 2022 harvest with a grape stomp! Sip on a harvest tasting of 3 new wines, learn about the different grape varietals we grow in the… Continue Reading Grape Stomp

Recurring

Utilities Commission Meeting

Town of Chesterotwn 118 N. Cross Street, Chestertown, MD

3/28/2022 - Town Council meetings will now start at 6pm CLICK FOR TOWN AGENDAS & MINUTES

Cars on High

300 High Street - Fountain Park

Come on out to Cars On High St. in Chestertown, MD to show off your Exotic, Classic or Vintage car on the 3rd Thursday of the month, April thru October.

Grape Stomp

Crow Vineyard & Winery - 12441 Vansants Corner Road

Join us in celebrating our 2022 harvest with a grape stomp! Sip on a harvest tasting of 3 new wines, learn about the different grape varietals we grow in the… Continue Reading Grape Stomp

Emmanuel Episcopal Church Organ Series

Emmanuel Church - 101 North Cross Street by the Fountain Park

Jeffrey Brillhart is Director of Music and Fine Arts at Bryn Mawr Presbyterian, PA, and on the music faculty of Yale University where he teaches organ improvisation.

Chestertown Car Show

Downtown Chestertown - High Street, Chestertown - Downtown Chestertown - High Street, Chestertown

Register your own pride and joy to compete for trophies, or just stroll the street to admire what other auto enthusiasts have brought to display, from custom hotrods to classic… Continue Reading Chestertown Car Show

Touch A Truck Ag Fest

Kent County Ag Center - 21349 Tolchester Beach Rd, Chestertown, MD 21620

Come out to the Ag Center and explore emergency vehicles, construction and farm equipment, trucks and more! Fun Family Event!

Recurring

HP Fest

Downtown Chestertown-Various - 200 Block of High Street

A Weekend of Magic: Grab your wand, hop on your broom, and come for a weekend of magic at the fifth annual Chestertown HP Festival. Explore our colonial river town… Continue Reading HP Fest

Cars on High

300 High Street - Fountain Park

Come on out to Cars On High St. in Chestertown, MD to show off your Exotic, Classic or Vintage car on the 3rd Thursday of the month, April thru October.

Emmanuel Episcopal Church Organ Series

Emmanuel Church - 101 North Cross Street by the Fountain Park

Gabriel Benton is the organist at Grace United Methodist Church, Wilmington, DE. He is a graduate pf the Oberlin and Julliard Conservatories and the Yale Institute of Sacred Music.

Festival Grand Opening

Raimond Cultural Center - 101 Spring Avenue - Raimond Cultural Center - 101 Spring Avenue - Raimond Cultural Center - 101 Spring Avenue - Raimond Cultural Center - 101 Spring Avenue

A Festival Grand Opening of the Kent Cultural Alliance's new home, the Vincent and Leslie Prince Raimond Cultural Center. Music, art, food trucks, and celebration More INFO soon. Times shown… Continue Reading Festival Grand Opening

Recurring

Dickens of a Christmas 2022

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! For a full schedule, ticket sales, and more information, visit https://mainstreetchestertown.org/dickens/

Chestertown Art Walk

Chestertown A&E District - Downtown Chestertown

Come to the Chestertown Arts & Entertainment District’s ART WALK. Dozens of artists and artisans will be selling works at galleries, storefronts, restaurants and around town. Live music will also… Continue Reading Chestertown Art Walk

Emmanuel Episcopal Church Organ Series

Emmanuel Church - 101 North Cross Street by the Fountain Park - Emmanuel Church - 101 North Cross Street by the Fountain Park

Katherine Johnson is an organ performance student at the Oberlin Conservatory, where she studies with Christa Rakich.

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