Courtesy of Shanty Grill

Dock & Dine: One Cruiser’s Faves

It’s the time of year when dining al fresco takes on an entirely different meaning, as restaurants up and down the Bay become meccas for outdoor gatherings. And one of the best secrets is the ease with which you can navigate the Chesapeake to find some of the best restaurants. Some are dive bars with fried food in red plastic baskets; others are formal restaurants with white linens and extra forks. In reviewing restaurants for this issue, we focused specifically on whether or not the establishment would pass the muster of a local. 

It’s because there’s a significant difference between the palates of “from heres” and “come heres.” Locals shudder should a crabcake ever be overcooked; families are judged upon whether there’s J.O. Spice or Old Bay on the table. And there’s absolutely no substitute for rockfish, ever. 

Up and down the Bay, we found restaurants of all classes and calibers that made us excited to get out on the boat and enjoy dinner together. Wherever you are, take the opportunity to bring together friends and family and enjoy the bounty that is Chesapeake cuisine. 

Dock of the Bay

9025 Cuckold Point Rd., Sparrows Point, Maryland

It’s important to have a restaurant that knows two things: food should taste good, and it should be affordable. Luckily, Dock of the Bay, just off Hart Miller Island understands this. Mushroom caps are stuffed with crabcake; the rockfish bites appetizer could be an entire meal. If the views toward the Eastern Shore aren’t relaxing enough, a playground for the little ones gives you a moment of respite from the chaos of the cockpit before you head back out.

Steamed Mussels at Carson’s Creekside. Photo courtesy of Carson’s Creekside

Carson’s Creekside 

1110 Beech Dr., Middle River, Maryland

There’s so much to be said for upscale dining with a side of down-home charm. And that’s what you get at Carson’s, which bills itself as a casual bar with water views. The seafood is more along the lines of stuffed rockfish and the steak is filet, but there’s also ribs and chicken, fried green tomatoes, and, of course, crabs to be had. If Middle River isn’t a big destination for you when cruising the Upper Bay, Carson’s is going to change that.  

Nick’s Fish House

2600 Insulator Dr., Baltimore, Maryland

Nick’s Fish House on the Patapsco has been a mainstay in Baltimore for ages. Known for its great views and its excellent beverages, it’s fun in the sun with fish on a bun. But within the last few years, the menu has taken some big steps away from the standard pub fare you often expect to find. Options for steamed shellfish abound, as well as upscale sandwiches and delicious homemade sides. If you’re there for happy hour, a smaller menu offers bar favorites at very reasonable prices. 

The Shanty Beach Bar

21085 Tolchester Beach Rd., Chestertown, Maryland

If you live on the Western Shore, taking your boat to Ocean City for some beach bar excitement is a bit of a hike. Luckily there are a few beach bars on Maryland’s Eastern Shore that offer a similar tiki bar vibe, and thankfully without the steep resort prices. The Shanty Beach Bar, nestled in Tolchester Marina, can be reached by car, but most everyone comes by boat. There’s almost always live music and a sunset to be had, and we love the fact that you can be barefoot at the bar. Don’t go if you aren’t into having fun. 

The Harbor Shack

20895 Bayside Ave., Rock Hall, Maryland

Consistency is a big thing when it comes to your favorite restaurant. Perhaps that’s part of the appeal of The Harbor Shack, Rock Hall’s local dockside bar and restaurant, which is a mainstay for locals who know where to eat in town. The meticulous kitchen staff is the same every shift, and the quality always exceeds the price on the bill. We recommend ordering the Caribbean Rum Bucket and a spread of seafood appetizers and enjoy the scene before getting on your boat and heading back home. 

Nanny’s Deviled Eggs with Crab at The Point Crab House. Photo courtesy of Crab at The Point Crab House

The Point Crab House and Grill

700 Mill Creek Rd., Arnold, Maryland

The Magothy River offers some of the most peaceful cruising on the Chesapeake. Long, idyll stretches punctuated by hidden creeks and coves offer a respite from the Bay itself. And luckily, one of the area’s best restaurants exists on Mill Creek next to Ferry Point Marina. The Point Crab House and Grill takes casual dining up a level with a modern twist on some Southern comfort food favorites. Vegetables and seafood are always fresh and in-season, and dishes are imaginative and beautiful at the same time. „

The Pier Oyster Bar and Grill

48 South River Rd. S, Edgewater, Maryland

The South River is a great place to find a quiet cove and tuck in for the night. Thankfully, there’s an excellent restaurant that makes it easy to find an excuse to not add “cooking dinner” to your evening. The Pier has a great outdoor area (heated during cooler months) with a big playground. Food is no-fuss and delicious—fish sandwiches are the stars of the show. The Pier is a great place to bring your parents and your kids alike: everyone can have a great time. 

Steamer Platter at The Choptank. Photo courtesy of The Choptank

The Choptank

110 Compromise St., Annapolis, Maryland

One of the most exciting new restaurants in Annapolis is The Choptank, a beautiful restaurant that opens directly onto Ego Alley and the harbor. While the Choptank doesn’t have its own dock, you can call ahead to Oasis Marina and secure a slip for your reservation. The Choptank’s menu is full of classics with fine dining twists, but little elements work to elevate the cuisine to near perfection. Whether you’re looking to impress someone or be impressed yourself, the Choptank is the perfect spot.  

Sushimi Tuna Tower at Libbey’s Coastal Kitchen. Photo courtesy of Libbey’s Coastal Kitchen

Libbey’s Coastal Kitchen

357 Pier One Rd., Stevensville, Maryland 

Libbey’s Coastal Kitchen at the Bay Bridge Marina is a phenomenal stopping point for Middle Bay adventures. Located at the base of the Chesapeake Bay Bridge’s eastern edge, Libbey’s offers docking for diners at no extra cost and has great Adirondack chairs, games for kids, and a great menu of food and drinks to get you ready to head back out. A cozy patio upstairs makes the whole place feel more like a yacht club than a restaurant, especially with the beautiful sunset views. Prices, however, remain very reasonable. 

Oysters Rockefeller at The Narrows. Photo courtesy of The Narrows

The Narrows 

3023 Kent Narrow Way, Grasonville, Maryland

For the last 30 years, this family-owned restaurant has been offering Eastern Shore cuisine at its absolute best. It’s hard to order anything other than crab (the cream of crab soup comes with additional sherry), but many of the non-seafood options will remind you of a favorite steakhouse. Docking is available on site, and you’ll see that many other diners are also taking the boat out for the day. This is one way to make a simple joyride exceptionally memorable. 

Grilled Shrimp Skewer at Foxy’s Harbor Grille. Photo courtesy of Foxy’s Harbor Grille

Foxy’s Harbor Grille

125 Mulberry St., St. Michaels, Maryland

The great thing about Foxy’s is that finding it by land could be considered a little tricky. Off the beaten path of Talbot Street and a hop, skip and a paddle from the Chesapeake Bay Maritime Museum, Foxy’s is accessible by water (and water taxi) and offers great cool drinks and welcome shade after a day on the boat. Their menu includes an extensive listing of crushes, and food offerings are easy and delicious, reminiscent of your favorite beach bar in the islands.

Tiki Bar & Grill Solomons

85 Charles St., Solomons, Maryland

You don’t have to be a St. Mary’s College graduate to have a story about getting stupid at the Tiki Bar. But you also don’t have to be freshly 21 to enjoy this fantastic destination point in Solomons. The environment is chill, leaving plenty of places to settle in and enjoy the scene without having to stake out a place at the bar all night. And the menu runs everywhere from seductively simple crab dip with tortilla chips to fancy-pants Korean beef skewers with rice and vegetables. While the Tiki Bar is still our favorite place to unwind after a hot day of Southern Bay Race Week sailing, it’s also a great place to grab lunch with friends. 

Charles Street Brasserie

120 Charles St., Solomons, Maryland

We get it: seafood isn’t for everyone. And burgers are great, but sometimes you want something different. The Charles Street Brasserie in Solomons is a welcome addition, offering tapas (small plates) that reflect both Spanish influences and American classics. The restaurant itself is quaint and romantic, if your boat doesn’t exactly offer ambience. There’s a piano brunch on Sundays and great weekly specials to make your bill a little lighter. And there’s also great seafood. 

Ruddy Duck Seafood and Alehouse

16800 Piney Point Rd., Piney Point, Maryland

Craft beer and fresh, local oysters. What more do we need to say? This gem on St. George’s Island brings a lot to the table, doing classic seafood right and without fussiness. Prices won’t break the bank, and the quality of dishes and excellent service always make for a memorable experience. Seating on the deck isn’t exactly plentiful, so grab takeout and head back to your boat to enjoy some of the best views St. Mary’s County has to offer. 

Reedville Market

729 Main St., Reedville, Virginia

There’s a distinctive, quiet calm in Virginia’s Northern Neck peninsula, with small seaside towns bringing a unique charm to the area you can’t find anywhere else. At Reedville Market, which gets its name from the fact that it used to be the town’s lone general store, you can find excellent steak, seafood, and scenery. Because the restaurant is one of the better dining establishments on the peninsula, it’s worth it to call ahead for a reservation. Coming down from Solomons or across the Bay from Tangier, Reedville Market offers tasty food in a very peaceful setting. 

Panna Cotta at Merroir. Photo courtesy of Merroir


784 Locklies Creek Rd., Topping, Virginia

The Rappahannock River is a hotbed for oysters, and Merroir has the best ones. As an arm of the Rappahannock Oyster Company, Merroir bills itself as a “tasting room” rather than a restaurant per se. Tables extend into the sandy beach offering an open atmosphere, and a menu that comes practically directly from the water you’re gazing out upon. The menu itself is innovative. Oyster stuffing is baked into a muffin and topped with a cream sauce; smoked trout dip is served with a side of naan. Merroir is unpretentious and a lot of fun for oyster connoisseurs and families alike. Reservations aren’t accepted, but since there are limited boat slips available, it’s best to call ahead and make sure you have a place to stow your craft while you dine. 

The Shanty

33 Marina Rd., Cape Charles, Virginia

Why we have to go all the way to the mouth of the Bay for this favorite spot, we’ll never understand. But The Shanty is everything you want in a dock bar: excellent catch of the day, great beverages, and food you can eat in one hand while you take a picture of the water with the other. Fish is always off-the-boat fresh and from local suppliers, and the fries are scattered with Old Bay. It’s restaurants like this that make you fall in love with living on the Chesapeake all over again. 

MacDuff Perkins lives in Annapolis, where she is the owner of Groundswell Yoga Studio. She and her family enjoy sailing their Sabre 42 around the East Coast.