Things to do in Chestertown
Food & Drink
Marylands Chestertown Farmers & Artisans Market
118 North Cross StreetEvery Saturday 8-12pm.
Best pastries in town. Don’t leave without trying a Sun Bun! Also fresh baked bread, artisan style sandwiches and great coffee. Eat in or outside. Closed Mondays
37 locals recommend
Evergrain Bread Company
201 High StBest pastries in town. Don’t leave without trying a Sun Bun! Also fresh baked bread, artisan style sandwiches and great coffee. Eat in or outside. Closed Mondays
Play It Again Sam
108 S Cross StGreat patio Outback. Artisan sandwiches. Barista coffee
Great food and great atmosphere. On the Sassafras River I’m Galena.
6 locals recommend
The Granary Restaurant
100 George StGreat food and great atmosphere. On the Sassafras River I’m Galena.
Stone baked oven pizza and fresh pasta dishes. Good wine selection, Eat in or take out. Nice atmosphere in Restaurant. Traditional Italian family owned.
27 locals recommend
Luisa's Cucina Italiana
849 Washington AveStone baked oven pizza and fresh pasta dishes. Good wine selection, Eat in or take out. Nice atmosphere in Restaurant. Traditional Italian family owned.
Imported Cheese, Wine, Pate, and wonderful charcuterie platters for special occasions. Going out for the day? Call ahead and let them prepare a picnic for you!
22 locals recommend
Chester River Wine & Cheese Co.
117 S Cross StImported Cheese, Wine, Pate, and wonderful charcuterie platters for special occasions. Going out for the day? Call ahead and let them prepare a picnic for you!
BAD Alfred's Distilling
323 High St
The Kitchen at the Imperial
208 High St
Watershed Chestertown
337 High StreetBest Pizza, by the slice or whole pie. Salads, pasta, and more. Eat in or take out. No delivery
15 locals recommend
Procolino's Pizza
711 Washington AveBest Pizza, by the slice or whole pie. Salads, pasta, and more. Eat in or take out. No delivery
Pop up Tapas bar and restaurant. Not open every day so call ahead. Great atmosphere and paella!
13 locals recommend
Casa Carmen Wines
312 Cannon StPop up Tapas bar and restaurant. Not open every day so call ahead. Great atmosphere and paella!
Stam's Luncheonette
Best for light fare and homemade ice cream!
If your looking for crabs, look no further! Great retail location for pick up. Steamed or live, by the bushel or less. Also homemade pastas, and sides.
Clark Seafood
23242 Handy Point RdIf your looking for crabs, look no further! Great retail location for pick up. Steamed or live, by the bushel or less. Also homemade pastas, and sides.
Sugar Doodles Sweet Shop
Ice cream and sweet treats!
Sightseeing
Tolchester Marina Inc
21085 Tolchester Beach Rd
Sultana Education Foundation
200 S Cross StThey do group sightseeing charters on the Chester River. Check their Calendar. Great Brunch and sunset cruises with open bar and catered food. Open too boat upstairs for best views, restaurant style seating downstairs
12 locals recommend
Chester River Packet Company
They do group sightseeing charters on the Chester River. Check their Calendar. Great Brunch and sunset cruises with open bar and catered food. Open too boat upstairs for best views, restaurant style seating downstairs
Live auction every other Wednesday. Inside and outside. From jewelry to furniture and much much more!
Dixon's Furniture Auction
2017 Dudley Corner RdLive auction every other Wednesday. Inside and outside. From jewelry to furniture and much much more!
Garfield Center for the Arts at the Prince Theatre
210 High St
Crow Vineyard & Winery
12441 Vansant Corner Rd
Chestertown Marina LLC
207 S Water St
Blue Crab Chesapeake Sailing Charters
21055 W Sharp St
Wilmer Park
413 South Cross StreetShopping
Wonderful eclectic gift shop. Books, cards, clothing, and unique gifts and decor. Do not miss while in Chestertown!
12 locals recommend
Twigs & Teacups
111 S Cross StWonderful eclectic gift shop. Books, cards, clothing, and unique gifts and decor. Do not miss while in Chestertown!
The Finishing Touch
311 High St
Mimi's Closet
307 High St
Bee Crafty Collectibles
335 High Street
Bloomin' Wild Florist
Figg's Ordinary
207 S Cross St
The Mill of Kingstown
Anthony's Flowers
Bohemia Trading Company
7400 Church Hill Rd