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1. Admiral's Beachside Bar

 Rock Hall, Maryland
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2. Arby's of Chestertown

 Chestertown, Maryland
Roast beef sandwiches and more in a quick, convenient manner.
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3. Bad Alfred's Distillery

 Chestertown, Maryland
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4. Bespoke Chocolate

 Chestertown, Maryland
Your destination in Chestertown, MD, for chocolate and other sweet treats! Enjoy truffles, fudge, fresh roasted nuts, and chocolate delights of all sorts. Plus: Special events, custom chocolate designs, and more.
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5. Blue Heron Oyster House & Inn

 Rock Hall, Maryland
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6. Bluebird Tavern

 Chestertown, Maryland
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7. C-Town Deli & Liquor Store

 Chestertown, Maryland
Proudly serving Chestertown for over 30 years! Exclusively serving Boar's Head in the deli. Soups and salads are also available.
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8. Cafe Sado

 Chestertown, Maryland
Serving sushi and authentic Thai cuisine.
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9. Casa Carmen Wines

Serving wine and tapas, our Bodega & Tasting Room in downtown Chestertown, MD, is created in the spirit of the traditional wine bodegas of Spain and South America — an unpretentious place to drink well, eat well, and enjoy good company.
 Chestertown, Maryland
Come and try small-lot craft wines and vermouth accompanied by gourmet cheese and charcuterie boards, Spanish-style tapas, and small plates.
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10. Chester River Seafood

 Rock Hall, Maryland
Specializing in River Crabs! We offer Crabs(live or steamed) - Soft Crabs - Scallops - Assorted Fish - Clams - Oysters - And More.
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11. Chester River Wine & Cheese Co.

 Chestertown, Maryland
Chester River Wine & Cheese Co. is a retail store specializing in wine, cheese, olives, cured meats, pate, and other gourmet specialty provisions. We also offer wine by the glass, cheese and charcuterie boards for onsite consumption.
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12. Chester River Yacht & Country Club

 Chestertown, Maryland
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13. China House

 Chestertown, Maryland
Authentic Chinese food to eat-in or carry out.
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14. Clark's Seafood

 Chestertown, MD
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15. Crow Vineyard, Winery & Inn

Sip Stay See Savor
 Kennedyville, Maryland
Enjoy a unique farm experience: walk the trails on our 365 acre farm, enjoy views of the vineyard, experience a wine tasting, stay in our Inn...about an hour from Philadelphia, Baltimore, Washington DC, minutes from Chestertown.
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16. Deep Blue at Kitty Knight

 Galena, Maryland
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17. Dockside Cafe on Rock Hall Harbor-Open Memorial Day through Labor Day Only

 Rock Hall, Maryland
Situated in a restored fish shack, the Dockside Café offers only the freshest seasonal ingredients to create some very eclectic fare. Herbs, tomatoes and veggies are grown on the premises.
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18. Domino's Pizza

 Chestertown, Maryland
Domino's pizza made and delivered fresh every day!
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19. Double Tap Tavern

All roads lead to Golts.
 Golts, United States
A great “local” bar! No pretense - just fun people, good food, pool table and music.
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20. Dunkin' Donuts

 Chestertown