Waterfront Dining in Anne Arundel County Off the Beaten Path

When the urge to dine al fresco strikes in Anne Arundel County, it’s easy to head to the obvious spots — many of which are located along the Annapolis waterfront, including Pusser’s Caribbean Grille, Blackwall Hitch, and Carrol’s Creek Cafe

That’s a shame, because there are many other places in the region where you can enjoy a peaceful meal outdoors, which are just as tasty but less well-known.

Below are two waterfront dining options in Annapolis that are far removed from the hustle and bustle of downtown. They are two gems in vibrant neighborhoods that most tourists don’t know about.

The bar on the dock at Pirate Coves restaurant in Galesville, on the West River.
The bar on the dock at Pirates Cove restaurant in Galesville, on the West River. (Robin Daumit)
  • 4817 Riverside Drive, Galesville

Drive south of Annapolis about 14 miles to the historic village of Galesville, a village dating back to the mid-1600s, and discover a gem on the West River.

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Although Pirates Cove Restaurant was first established in 1960 in what was already a bustling yachting and sailing hub on the West River, it was Bob Platt, former owner of Mums Restaurant on Annapolis’ City Dock, who in 1984 created the Pirates Cove we know today, with an inn, dockside bar and marina. He no longer owns the restaurant, having sold it in 2015, but his influence remains.

Take a break for a couples dinner at the Dock Bar and Dining Area while listening to live music or halyards hitting yacht masts in the evening breeze. Or settle in at their large dining pier with friends and family for a seafood dinner

They also serve traditional country fare such as liver and onions and several chicken options. I also recommend the Irish Dexter beef burger or the traditional fish and chips platter.

Once across the South River, the bustling pace of Annapolis quickly gives way to a drive through the countryside, making Pirates Cove the perfect dining destination to “get away from the herd.” Boaters can call ahead for a nightly dock rental.

Enjoy the summer breeze while dining al fresco at Harper's Waterfront in the historic area of ​​Turkey Point, a small island 12 miles south of Annapolis.
Enjoy the summer breeze while dining al fresco at Harper’s Waterfront in the historic area of ​​Turkey Point, a small island 12 miles south of Annapolis. (Robin Daumit)
  • 1107 Turkey Point Road, Edgewater

New to the scene in the historic area of ​​Turkey Point, a small island 12 miles south of Annapolis, is Harper’s Waterfront, a dining establishment with a wow factor. It’s as chic and modern as a big-city restaurant.

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Owner Todd Harper has been in the food business for years with a casual dining nightclub, and meanwhile has big dreams of opening a more upscale casual dining restaurant on the water. Friend and chef Brian Thornton helped him make this dream a reality. .

Come to Turkey Point to dine on the deck, where you’ll often feel the summer breeze. Try a shareable platter of drunken mussels and pickled deviled eggs, paired with a refreshing Sonoma chardonnay. Or try a Wagyu burger, piled high and cooked to perfection, with a matching bottle of red.

With ample parking and endless inspiring views of the quiet marina life from the second-story deck, it’s easy to imagine the days when steamboats plied these waters to escape the hustle and bustle of city life. Harper’s modern design and stylishly appointed ambiance features convenient elevator access directly from the parking lot to the restaurant and complimentary dockage for restaurant guests on a first-come basis.

Guests at Chessie's Wharf can enjoy 38 beers on tap while seated at a solid wood picnic table on a deck overlooking the water.
Guests at Chessie’s Wharf can enjoy 38 beers on tap while sitting at a solid wood picnic table on a patio overlooking the water. (Robin Daumit)
  • 609 Melvin Ave., Annapolis

The recently opened Chessie’s Wharf in West Annapolis, just two blocks from the Navy-Marine Corps Memorial Stadium, is no stranger to the craft beer movement. The Cambridge brewery has been around since 2013.

With over 38 impressive draft beers to choose from in the Annapolis tap room, the place to be from March through October is outside on their beautifully designed, covered, airy dining patio with solid wood picnic tables. The outdoor heating system means cozy outdoor dining even in the cool March temperatures.

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Dishes to try include the lobster, the Chessie chop — a shaved ribeye with peppers and onions — and the delicious beer cheese on a sub bun, served with a richly flavored India pale ale and a Bucktown brown ale. The food and drinks here were so good that I returned a second time and tried the restaurant’s award-winning crab cake, along with an American blonde ale and a double IPA. It was a delightful experience.

The al fresco dining experience here is spacious with a setting that makes you feel like you’re relaxing on your own patio in your own backyard. And if you’re not a beer drinker, don’t worry, Chessie’s Wharf has a variety of fun mocktails to choose from.

Forward Brewing and Restaurant in historic Eastport is known for its waterfront dining and seasonal menu featuring locally sourced ingredients.
Forward Brewing and Restaurant in historic Eastport is known for its waterfront dining and seasonal menu featuring locally sourced ingredients. (Robin Daumit)
  • 418 Fourth Street, Annapolis

Forward Brewing and Restaurant is Annapolis’ only on-premise brewery, tucked away in the streets of the historic Eastport neighborhood in what was once a family home for 30 years. Claire and Cam Bowdren, who met at another iconic Eastport restaurant, Vin 909, own and have transformed the building.

The brewery has grown into a place where locals and tourists alike gather for the perfect beer and an informal meal outside on the veranda or on the second terrace with 50 seats.

Forward’s approach is to serve ethical and local ingredients in their seasonal menu. They are also one of the few restaurants in Annapolis certified by the Maryland Department of Agriculture to serve only freshly harvested crabs.

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For beer connoisseurs, there’s an impressive collection. A specially created brew designed earlier in the spring, Oak and Stone, is a light German ale that’s been conditioned while fermenting on toasted French oak staves. It has vanilla-oak qualities. There are also kettle sours for the summer, a honey brown ale, dark beers with dark chocolate and Maryland-grown hops.

The food isn’t bad either: homemade pretzels, pretzel pizza, sea bass ceviche, smoked fish spread, and tacos of all shapes and sizes.

If you’re looking for a “real” outdoor dining experience, Forward Brewing has a 1.5-hour excursion on their 30-foot, six-passenger crabbing boat that includes a pack of Forward beer and a Snackle box of snacks.

Robin Daumit is an Annapolis-based freelancer who has competed on several Food Network competitions, as well as PBS’ “The Great American Recipe,” and is the content creator behind @WhiskandDine.

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