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Admiral's Beachside Bar

1. Admiral's Beachside Bar

 Rock Hall, Maryland
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Bay Wolf Restaurant

2. Bay Wolf Restaurant

 Rock Hall, Maryland
Austrian and Eastern Shore cuisine. Located in the heart of Rock Hall within easy reach of Marinas. Local pick-up available.
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Cafe Sado

3. Cafe Sado

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

4. 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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Chester River Yacht & Country Club

5. Chester River Yacht & Country Club

 Chestertown, Maryland
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Dockside Cafe on Rock Hall Harbor-Open Memorial Day through Labor Day Only

6. 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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Double Tap Tavern

7. 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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Galena Pizzeria

8. Galena Pizzeria

 Galena, Maryland
Great Italian food in a friendly atmosphere.
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Inn at Osprey Point, Marina, and Restaurant

9. Inn at Osprey Point, Marina, and Restaurant

 Rock Hall, Maryland
At Osprey Point Inn, Restaurant and Marina, you'll experience the perfect fusion of luxurious accommodations, elegant dining, and a relaxed and friendly environment.
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Kitchen at the Imperial, The

10. 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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La Cascada Restaurante

11. La Cascada Restaurante

La Cascada is a local restaurant serving both American and Traditional Latin Dishes. The Latin portion of the menu is heavenly inspired from Guatemalan Cuisine and Recipes.
 Millington, Maryland
La Cascada is a local restaurant serving both American and Traditional Latin Dishes. The Latin portion of the menu is heavenly inspired from Guatemalan Cuisine and Recipes.
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Luisa's Cucina Italiana

12. 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.
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Modern Stone Age Kitchen

13. Modern Stone Age Kitchen

 Chestertown, Maryland
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Molly's Restaurant

14. Molly's Restaurant

 Kennedyville, Maryland
For decades the corner of MD 213 & 298 has been a mecca for locals and visiting hunters alike. Molly’s Restaurant serves home-style cooking featuring local ingredients and recipes steeped in Eastern Shore traditions. Open 7 days a week.
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The Channel Restaurant at Tolchester Marina

15. The Channel Restaurant at Tolchester Marina

 Chestertown, Maryland
We offer a full service menu. Our restaurant has long had a reputation for the best crab cakes on the Bay. Seasonal operation.
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The Retriever

16. The Retriever

 Chestertown, Maryland
The Retriever is a bar featuring oysters and other victuals. We do have a dining area which is open seating from 5:00pm to 8:30pm. Please note, we are bar which means that everyone must be at least 21 years old to enter the building.
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Uncle Charlie's Bistro

17. Uncle Charlie's Bistro

 Chestertown, Maryland
Uncle Charlie's Bistro offers a full lunch and dinner menu, as well as weekly specials featuring the finest cuisines offered on Maryland's Eastern Shore.
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Watershed Alley

18. Watershed Alley

 Chestertown, Maryland
Watershed features the bounty of the Chesepeake watershed region: the Chester River, Chesapeake Bay, Atlantic Ocean, and local farms and fields—clean, simple, authentic regional food “from the watershed to the Watershed".