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1. Blue Heron Oyster House & Inn

 Rock Hall, Maryland
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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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3. Deep Blue at Kitty Knight

 Galena, Maryland
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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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5. Evergrain Bread Company

 Chestertown, Maryland
Evergrain Bread Company specializes in artisan breads and pastries crafted in the European tradition.
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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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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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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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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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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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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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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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13. Passages Bar & Grill

 Rock Hall, Maryland
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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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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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16. The Shanty Beach Bar

 Chestertown, Maryland
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17. Two Ten Chestertown

 Chestertown, Maryland