EXPLORE OUR Chestertown Businesses Downtown Chestertown has Something for Everyone AllAccommodationsArt + GalleriesDiningHealth, Beauty + WellnessLegalProvisionsReal EstateServicesShoppingWorship Angela’s CottageShopping Bad Alfred’s Distilling Co.Dining, Kid Friendly Bart’s RecordsShopping Bee Crafty Antiques & CollectiblesKid Friendly, Shopping Bespoke ChocolateKid Friendly, Shopping Big Mixx’s Beautiful BeginningsHealth, Beauty + Wellness, Kid Friendly, Services Bloomin’ WildServices, Shopping Boyer’s JewelersShopping Brampton Bed & BreakfastAccommodations C-Town LaundromatServices Casa CarmenDining, Kid Friendly Cat ColloquiumNon-Profit, Services Chesapeake Bank & TrustBank, Services Chester River FriendsWorship Chester River Packet CompanyDining, Kid Friendly Chester River Wine & CheeseServices, Shopping Chestertown ElectricShopping Chestertown MarinaServices Chestertown Natural FoodsProvisions, Shopping Christ United Methodist ChurchWorship Coco’s Pet CenterKid Friendly, Services, Shopping Coldwell BankerReal Estate, Services Cookerly & BarrollLegal, Services Cross Street RealtorsReal Estate, Services Dixon’s Auction at CrumptonServices, Shopping Dollar GeneralShopping Doug Ashley RealtorsReal Estate, Services Duke LawLegal, Services Eastern Shore Urgent CareHealth, Beauty + Wellness, Services Emmanuel Episcopal ChurchWorship Empty Hangers Consignment BoutiqueKid Friendly, Shopping Evergrain Bread CompanyDining, Kid Friendly, Shopping First United Methodist ChurchWorship Flow Salon SpaHealth, Beauty + Wellness, Services Garfield Center for the ArtsArt + Galleries, Kid Friendly Great Oak ManorAccommodations Hegland GlassArt + Galleries, Shopping Houston’s Dockside EmporiumShopping Inn at Mitchell HouseAccommodations Janes United Methodist ChurchWorship JBK Ace HardwareShopping Kent County Family YMCAHealth, Beauty + Wellness, Kid Friendly, Services Kent County NewsServices MacLeod Law GroupLegal, Services Massoni Art GalleryArt + Galleries Mimi’s ClosetServices, Shopping Modern Stone Age KitchenDining, Kid Friendly Music LifeKid Friendly, Shopping Nearly NewShopping Occasions CateringServices Park Row FloatsServices Phat Daddy’s BBQDining, Kid Friendly Play it Again SamDining, Kid Friendly Rasin, Wootton & HurdLegal, Services River LivingShopping RiverArtsArt + Galleries, Kid Friendly, Services Riverside UniqueShopping Robert Ortiz StudiosArt + Galleries, Shopping Robert Ortiz StudiosArt + Galleries Sacred Heart Catholic ChurchWorship Sarah Paige Studio SalonHealth, Beauty + Wellness, Services Select Land and HomesReal Estate, Services Silver LiningsShopping Spa AngelsHealth, Beauty + Wellness, Services Stam’s LuncheonetteDining, Kid Friendly Sugar Doodles Sweet ShopDining, Kid Friendly The Artists’ GalleryArt + Galleries The BankServices The BookplateShopping The Finishing TouchServices, Shopping The Kitchen at the ImperialDining The Listening RoomShopping The Retriever BarDining The White Swan TavernAccommodations Tiny Tots BoutiqueKid Friendly, Shopping Twigs & TeacupsKid Friendly, Shopping Village HouseServices, Shopping Wadkovsky & MowellLegal, Services Walnut & WoolShopping Watershed AlleyDining Women in NeedShopping Zelda’s SpeakeasyDining Main Street Chestertown would not be possible without the support of our partners: