14 Dockside Restaurants Around the Chesapeake Bay Only Locals Know

Culinary Destinations
By Lena Hartley

Explore the hidden gems of the Chesapeake Bay with these 14 dockside restaurants known primarily to locals. Each offers a unique blend of fresh seafood and waterfront ambiance, providing a quintessential Maryland dining experience.

1. Cantler’s Riverside Inn

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Nestled on Mill Creek in Annapolis, Cantler’s Riverside Inn is where locals flock for authentic Maryland steamed crabs. Established in 1974, this no-frills crab house provides picnic-table seating by the water, creating a rustic yet charming dining experience.

Boaters often dock here, drawn by the promise of fresh blue crabs delivered directly to the dock. The bustling atmosphere and scenic views make each meal feel like a true Chesapeake Bay adventure.

Many visitors rave about the simplicity and flavor of the crabs, served with traditional Old Bay seasoning. It’s the kind of place that feels unchanged by time, offering a taste of Maryland’s rich crabbing history.

2. The Narrows Restaurant

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Known for its breathtaking views across Kent Narrows, The Narrows Restaurant is a prime destination for exceptional seafood. Its cream of crab soup and crab cakes are local legends, attracting both boaters and drive-up diners.

This dining spot offers a blend of elegance and comfort, with large windows framing the stunning seascape. Patrons often enjoy watching the boats cruise by as they indulge in expertly prepared dishes.

The Narrows is not just about the food; it’s a sensory experience that encapsulates the beauty of the Chesapeake Bay. The warm, welcoming atmosphere makes it a cherished retreat for those in search of culinary excellence.

3. Bridges Restaurant

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Perched over the scenic waters of Kent Narrows, Bridges Restaurant is celebrated for its deck-forward setting. Diners can savor fresh local seafood while enjoying spectacular sunsets, making it a favored spot for both locals and visitors.

The menu is a tribute to the bounty of the bay, featuring dishes crafted from the freshest catches. The relaxed yet vibrant atmosphere appeals to those looking for a perfect blend of fine dining and casual charm.

Bridges offers more than just a meal; it’s a gateway to the serene beauty of the bay, where each sunset paints a new masterpiece in the sky. This combination of great food and view creates an unforgettable experience.

4. Harris Crab House

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Harris Crab House in Grasonville is the quintessential family-owned crab house, a cornerstone of the local seafood scene. Known for its no-frills approach, it serves steamed crabs the Maryland way, complete with mallets and brown paper.

The lively atmosphere is filled with laughter and the sounds of cracking shells, drawing seasoned locals and curious newcomers alike. The views of the Kent Narrows bridge add to the charm, providing a picturesque backdrop.

This establishment has built its reputation on simplicity and quality, offering an authentic taste of Maryland. It’s not just a restaurant; it’s a place where memories are made over shared meals and stories.

5. Libbey’s Coastal Kitchen + Cocktails

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Libbey’s Coastal Kitchen + Cocktails in Stevensville offers a contemporary twist on bay-front dining. With large windows providing panoramic views of the Bay Bridge, this restaurant combines sophisticated design with a relaxed coastal vibe.

The menu is a delightful mix of elevated seafood dishes and inventive craft cocktails, appealing to those who appreciate a touch of elegance. The ambiance is perfect for both intimate dinners and lively gatherings.

Locals cherish this spot for its ability to blend modernity with tradition, serving up memorable experiences alongside impeccably prepared food. It’s a place where the Chesapeake’s heritage meets culinary innovation.

6. Waterman’s Crab House

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In Rock Hall, Waterman’s Crab House stands as a testament to Eastern Shore authenticity. This dockside gem offers a true maritime dining experience, complete with views of the peaceful harbor.

The weathered ambiance and live-water setting draw locals who swear by the seafood’s freshness and flavor. It’s a place where time seems to slow down, inviting diners to relax and enjoy.

Specialties like steamed crabs and crab cakes are local favorites, celebrated for capturing the essence of the bay. For those seeking genuine Eastern Shore charm, Waterman’s is a beloved fixture in the community.

7. The Pier Waterfront Bar & Grill

© Visit Maryland

Perched on the South River in Edgewater, The Pier Waterfront Bar & Grill offers a friendly dockside atmosphere. It’s a casual dining spot where boaters and land-goers mingle over seafood lunches and dinners.

The open-air deck provides a picturesque setting, perfect for enjoying the river views while savoring fresh catch. The relaxed vibe makes it a go-to for both locals and visitors seeking a laid-back experience.

The Pier’s appeal lies in its simplicity and charm, offering great food without pretense. Whether you’re arriving by boat or car, it’s a welcoming place to unwind and enjoy the beauty of the water.

8. The Crab Claw

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The Crab Claw, situated on the picturesque Miles River in St. Michaels, is a beloved spot for those seeking authentic Eastern Shore seafood. This historic building offers diners the chance to savor raw oysters and crab cakes as boats gently drift by.

Visitors appreciate the laid-back ambiance, complemented by the rich maritime history surrounding the area. The restaurant’s windows provide stunning views of the river, enhancing the dining experience with a sense of tranquility.

Famous for its steamed crabs, The Crab Claw remains a local favorite, capturing the essence of waterfront dining. Its commitment to tradition makes it a must-visit for seafood lovers exploring St. Michaels.

9. The Dock Restaurant

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Located in Chesapeake Beach, The Dock Restaurant is a lively dockside venue known for its vibrant atmosphere and stunning bay views. Diners enjoy outdoor seating right on the water, making it a popular choice for those seeking both scenery and seafood.

The menu features seafood towers and smash burgers, offering a delightful mix for all tastes. The lively setting ensures a fun dining experience, perfect for gatherings with friends and family.

The Dock’s charm lies in its ability to combine great food with a joyful ambiance, creating memorable moments by the bay. It’s a place where good times and delicious meals go hand in hand.

10. Dockside Restaurant & Sports Bar

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In Deale, Dockside Restaurant & Sports Bar offers a relaxed waterfront dining experience, combining fresh seafood with a casual bar atmosphere. It’s the perfect spot for sunset drinks and crabs, with a view of Rockhold Creek.

The laid-back vibe is complemented by nautical decor, creating a welcoming environment for both regulars and newcomers. The menu features a variety of seafood options, satisfying even the heartiest appetites.

Whether you’re a boating enthusiast or simply in search of good food and company, Dockside provides a warm, friendly setting. It’s a local favorite that captures the spirit of Chesapeake Bay living.

11. Foxy’s Harbor Grille

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Foxy’s Harbor Grille in St. Michaels is a vibrant spot where the Eastern Shore hospitality shines. With a lively deck overlooking the harbor, this restaurant attracts boaters and land-lovers alike.

The atmosphere is casual and inviting, with a menu boasting fresh seafood options that keep diners coming back. It’s a place where good food meets good company, creating a sense of community.

Foxy’s is not just a restaurant; it’s a staple of the local scene, where every meal feels like a celebration of the bay. Its charm and energy make it a must-visit for anyone exploring St. Michaels.

12. Skipper’s Pier Restaurant

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Deale’s Skipper’s Pier Restaurant is renowned for its relaxed waterside seating and standout seafood dishes. Known for oysters and crab-stuffed rockfish, it offers a taste of the southern Bay’s culinary delights.

The setting is rustic and inviting, with a deck that provides stunning water views. It’s a place where local flavors shine, making it a popular destination for seafood enthusiasts.

The charm of Skipper’s extends beyond the food, offering a warm and welcoming atmosphere that’s perfect for enjoying the beauty of the bay. It’s a beloved spot for savoring the essence of southern Maryland.

13. Bayard House

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Set in Chesapeake City along the C&D Canal, Bayard House offers historic charm with marina-side dining. This restaurant provides a unique view of the canal traffic, adding a touch of intrigue to your meal.

The menu features a variety of seafood options, allowing diners to enjoy fresh flavors in a picturesque setting. The building’s history adds depth, making it a fascinating place to dine.

Bayard House is perfect for those who appreciate both culinary excellence and scenic views. It’s a unique spot that combines the allure of history with the beauty of the water, offering a memorable dining experience.

14. The Granary/Fish Whistle

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Tucked away on the Sassafras River, The Granary and Fish Whistle offer a delightful twin experience of waterfront dining. Known for fresh catches and summer deck seating, these restaurants are a favorite among boaters.

The scenic backdrop of the river and surrounding greenery creates a peaceful ambiance, making it an ideal spot for a leisurely meal. The menu features a variety of seafood dishes, celebrating the local bounty.

Whether you’re docking for a quick bite or settling in for a long meal, these restaurants provide a refreshing escape. The combination of good food and beautiful views makes it a cherished haven on the river.