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1. Arby's of Chestertown

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

 Chestertown, Maryland
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3. 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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4. Bluebird Tavern

 Chestertown, Maryland
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5. 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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6. Cafe Sado

 Chestertown, Maryland
Serving sushi and authentic Thai cuisine.
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7. 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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8. 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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9. Chester River Yacht & Country Club

 Chestertown, Maryland
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10. China House

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

 Chestertown, MD
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12. Domino's Pizza

 Chestertown, Maryland
Domino's pizza made and delivered fresh every day!
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13. Dunkin' Donuts

 Chestertown
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14. Evergrain Bread Company

 Chestertown, Maryland
Evergrain Bread Company specializes in artisan breads and pastries crafted in the European tradition.
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15. Freeze, The

 Chestertown, Maryland
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16. Happy Chicken Bakery, LLC

 Chestertown
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17. Its Masala Time

 Chestertown, Maryland
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18. Kitchen at the Imperial, The

 Chestertown, Maryland
The Kitchen at the Imperial provides an award winning casual fine dining restaurant experience, in a unique, upscale atmosphere. Chef Steve Quigg (winner, Best Chef on the Eastern Shore 3 years in a row) and his staff pride themselves on their farm..
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19. Lands Point Winery & Vineyards

 Chestertown, Maryland
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20. Luisa's Cucina Italiana

 Chestertown, Maryland
Serving lunch and dinner daily, featuring Italian specialty entrees, gourmet pizzas and sandwiches in a casual dining atmosphere. Our dishes are prepared with locally grown fresh ingredients. Dine-in or carry out.