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Blue Heron Oyster House & Inn

1. Blue Heron Oyster House & Inn

 Rock Hall, Maryland
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Crow Vineyard, Winery & Inn

2. 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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Deep Blue at Kitty Knight

3. Deep Blue at Kitty Knight

 Galena, Maryland
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Double Tap Tavern

4. 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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Evergrain Bread Company

5. Evergrain Bread Company

 Chestertown, Maryland
Evergrain Bread Company specializes in artisan breads and pastries crafted in the European tradition.
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Fish Whistle at The Granary

6. Fish Whistle at The Granary

 Georgetown, Maryland
The Fish Whistle is moving from Chestertown to Georgetown overlooking the Sassafras River. Stay tunes for Grand Opening details.
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Harbor Shack

7. Harbor Shack

 Rock Hall, Maryland
Waterfront bar and grill serving seafood, steaks, and mexican. Casual atmosphere. Live music Saturday nights. Fun and upbeat - Great food!
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Java Rock

8. Java Rock

 Rock Hall, Maryland
Upscale, laid-back, gourmet coffee house with delicious lite fare. Boutique snacks, elegant and well-priced wines, and unique gifts.
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Kitchen at the Imperial, The

9. 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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Luisa's Cucina Italiana

10. 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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Molly's Restaurant

11. 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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Muskrat Alley Cafe

12. Muskrat Alley Cafe

 Rock Hall, Maryland
Eclectic blend of good food and fine shopping. Jewelry, books and specialty gifts. Shop while you eat a scrumptious healthy breakfast…it’s delightful!
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Passages Bar & Grill

13. Passages Bar & Grill

 Rock Hall, Maryland
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Play it Again Sam

14. Play it Again Sam

 Chestertown, Maryland
Located in the heart of downtown Chestertown, Play It Again Sam serves a complete line of coffee offerings, breakfast and lunch specialties, snacks and wine.
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The Landing at Great Oak

15. The Landing at Great Oak

 Chestertown, Maryland
Enjoy a casual dinner over looking Fairlee Creek. You can sit inside or outside on the covered deck. Traditional Eastern Shore cuisine, sandwiches, and light appetizers.
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The Shanty Beach Bar

16. The Shanty Beach Bar

 Chestertown, Maryland
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Two Ten Chestertown

17. Two Ten Chestertown

 Chestertown, Maryland