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Restaurants and Nightlife

49 West Coffeehouse, Winebar & Gallery

Just 35 minutes from Chesapeake Paradise, 49 West Coffeehouse, Winebar & Gallery in Annapolis offers fresh, simple dishes, desserts, and breakfasts in a cozy, artistic atmosphere. A local favorite for live music on weekends and Sunday afternoons, it’s a perfect blend of charm, culture, and comfort.

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Harry Browne's Restaurant

One State Circle downtown Annapolis just across from Capitol. Historic, elegant upscale ambiance (and maybe prices); good food including Sunday brunch. I love going there. A few tables outside.

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Ledo Pizza

Closest restaurant to here! Gourmet University of Maryland pizzas. Take a left onto RTE 256 at stop sign and go less than a mile--on your left in a little strip mall. 5720 Deale Churchton Rd, Deale, MD 20751

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Stan and Joes Riverside

Just 15 minutes from Chesapeake Paradise, Stan and Joe’s Riverside in Galesville sits at the end of a pier, serving whole crabs, classic bar fare, and cold drinks in a casual waterfront setting—open later than most spots nearby.

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Yellowfin Steak & Fish House

For a more upscale, romantic meal or 1/2 price happy hour seafood etc. with great views of the sunset! Just north of the South River Bridge on your way to Annapolis--about 20 minutes from here on Route 2.

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Dockside Restaurant & Sports Bar

Just a few minutes from Chesapeake Paradise, Dockside Restaurant & Sports Bar in Deale, Maryland, combines laid-back waterfront dining with stunning views of Rockhold Creek. Enjoy fresh seafood, classic American fare, and a lively sports bar atmosphere—perfect for relaxing with friends after a day on the Bay.

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Petie Greens

Just minutes from Chesapeake Paradise, Petie Greens Bar & Grill in Deale, Maryland, is a friendly local favorite known for its delicious steaks, hearty seafood, and welcoming vibe. Open on Mondays when many nearby spots are closed, it’s the perfect place to unwind and enjoy great food just a short walk from the marina.

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Always Ice Cream Company

Just 20 minutes from Chesapeake Paradise, Always Ice Cream Company in Edgewater serves up ultra-premium, handcrafted ice cream with over 250 rotating flavors, including vegan options. This family-friendly scoop shop is a local favorite for its rich flavors, generous portions, and welcoming atmosphere.

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Black Market Bakers

Just minutes from Chesapeake Paradise, Black Market Bakers is a local favorite in Deale, Maryland, serving handcrafted pastries, sandwiches, and coffee made fresh daily. Known for their famous cinnamon rolls, seasonal croissants, and artisan breads, it’s the perfect stop for a cozy breakfast or afternoon treat near the Bay.

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Killarney House

Located in the countryside of Davidsonville, Maryland, about 20 minutes from Annapolis, our restaurant offers great dining in a pine walled interior with high ceilings, antique farm tools decorating the walls, and colored glass reminiscent of Ireland's revered historic churches. In the warmer months we have outdoor dining surrounded by flowers and greenery on our bedecked porch, and when things are cooler you can request a table by the cozy fireplace in our main dining room. Live music & dance.

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