So you can enjoy the liquid lifestyle better, the pros at PropTalk have compiled and thoughtfully located some of the best Chesapeake Bay dock bars in Bay Country using this helpful interactive map of the Chesapeake Bay. A full list of dock bars follows farther down the page with helpful land-based directions and additional mapping tools. Always remember to take along a designated skipper/driver for your adventures, and if we missed your favorite dock bar spot, e-mail it to firstname.lastname@example.org and we’ll include it here.
For as much as we love our boat, we have one major problem: there’s never enough time to use it. Taking the boat out has become such a process. Packing the picnic, the kids’ toys, and all the essentials can make a six-hour tour look like we’re leaving the country for two weeks. A week of planning goes into a day’s cruise.
This summer we’re trying a different approach. We figure we have this boat, so why not use it more often? So to that end we’re instituting weeknight cruises to some of the best dock bars around the Chesapeake. Getting out on the boat doesn’t have to be about spending the entire day on the water: it can simply be about taking the boat across the Bay for a nice dinner. We want to catch some sunsets, and some sundowners.
This is going to be a summer to remember.
Hemingway’s Restaurant on Kent Island
The thing that we love the most about Hemingway’s dock bar is that you can leave Annapolis at 5:30 and be having your cocktail on their patio by 6:15. Located at the foot of the Bay Bridge and nestled next to the Bay Bridge Marina, this is one of our favorite places to watch the sun set. And we can’t get enough of the Rockfish Imperial. hemingwaysbaybridge.com
Pusser’s Caribbean Grille in Annapolis
It’s easy to fall in love with Pusser’s dock bar for their painkillers alone. The rum drink, that is. But Pusser’s is as good of a dock bar as it is a nice place for Sunday brunch. You can bring in the whole family to look out on the water, or you can saddle up to the bar solo for some quiet time out of the sun. It can get crowded during the weekend, so try it out during happy hour between 4 and 7 on weekdays. pussersusa.com
Rudee’s Dock Bar on the Inlet Virginia Beach, VA
Thirty years ago it was a bait and tackle shop, but today it’s one of the most popular dock bars in the lower Chesapeake. You can sit on the outdoor patio and cool off with the summer breeze just off the water, and the key lime pie is a sweet end to any day. The glider booths are a hit with kids, too. Transients are welcome at the Inlet Station Marina, and bring your beach towel to check out Virginia Beach before heading back home. rudees.com
Harbor Shack in Rock Hall, MD
Oh, the Crab Cake Stacker Sandwich, how we love you. But there’s a lot more to love about this downhome Shore Thing crab house. The glasses of wine are big, the beer is cold, and it’s so relaxing to have a seat on the deck of this dock bar and watch the water. They frequently have live music, which makes a great evening even better. harborshack.net
Smithfield Station, Smithfield, VA
You have to appreciate an upscale dock bar and restaurant created by two boaters themselves. Ron and Tina Pack were cruising the Bay with friends when they decided to plant roots in Smithfield, opening up a restaurant that serves some of the most delicious crab, flounder, and rockfishes dishes on the Bay, as well as some of the best views around. smithfieldstation.com
Bridges Restaurant and Dock at Kent Narrows/Grasonville
With 16 complimentary slips at this Kent Narrows hub, you can enjoy a delicious Chesapeake-inspired menu and a fantastic wine and beer list, all at reasonable prices. If you do end up staying overnight, slip fees are only $50, which gives you enough time to explore the area on foot. bridgesrestaurant.net
Paradise Ocean Club in Hampton, VA
While we love any restaurant that advertises a tiki lounge, this dock bar also come with a large outdoor swimming pool (there’s a baby pool for those who are just learning, too). After your swim, grab a quick shower and order your snacks. Sandwiches and entrees are not only tasty, they’re also very affordable (a pulled pork sandwich is $8, crabcake sandwiches are only $12). There’s something for the whole family at Paradise Ocean Club, so bring the whole brood. paradiseoceanclub.com
Pirates Cove on the West River, Galesville
Pirate’s Cove’s dock bar is a great place to hit on Wednesdays, when you can watch sailboat racing with a beer and a pile of steamed shrimp in front of you. Bring your boat over and have free slip fees as long as you have dinner at either the Cove or Big Mary’s Dock Bar, open Wednesdays through Sundays in the spring and summer. If you do spend the night, slips are only $40 for water, power, and showers. And did we mention the steamed shrimp? So good. piratescovemd.com
Thames St. Oyster House in Baltimore
Fells Point has some of our favorite restaurants around, that’s for sure. Thames Street Oyster House is relative newcomer that is becoming our favorite old standby. It’s always busy, so be ready to wait a bit for a table at this dock bar, but you won’t find better oysters in Baltimore. You can’t go wrong with the rest of the menu, for those of us who shun raw bivalves. We love the Grilled North Atlantic Albacore Tuna Sandwich and lobster roll, and usually find a reason to wander through the other pubs and gellaterias of Fells Point. thamesstreetoysterhouse.com
Cantler’s Riverside Inn in Annapolis
Cantler’s is a bit of an establishment in Annapolis. Their deck overlooking Mill Creek has been serving up some of the best crabs on the Chesapeake for almost forty years. Taking the boat over to Cantler’s dock bar is much more fun than driving, and the restaurant’s dock accommodates up to 10 boats with an addition beach for you to pull your tender, jet ski, or kayak up onto. The seafood is fresh daily, so we recommend calling ahead of time to hear what crabs they’re serving up. If your party has 10 or more in it, they’ll happily take a reservation. cantlers.com
Nick’s Fish House and Grill Baltimore, MD
If you’re in Baltimore and want to avoid the hustle and bustle of the Inner Harbor, head around Fort McHenry and Ferry Bar Park to Nick’s Fish House and Grill. The waterfront restaurant/dock bar has plenty of outdoor seating and a menu that will please everyone. Their blue crabs are some of the best in town, but there is also sushi, Chesapeake stand-bys like fried oysters, crab dip, and deck fries, and crab pretzels, and tasty burgers to enjoy after your time on the water. During the summer there is often a band on the deck to keep everyone entertained. nicksfishhouse.com
Harris Crab House in North Grasonville, MD
Calling around to crab houses, looking for the best prices per bushel will often lead you to Harris Crab House. But we really love them because of the care they take in preparing their seafood. All clams, oysters, fish, and shrimp are hand breaded and fried, and much of the seafood is caught directly from their docks. Owner Karen Oertal comes from a long line of watermen, so you can trust her with your seafood. And while the restaurant is just four minutes from the Bay Bridge, it’s much nicer to ride over in your boat. harriscrabhouse.com
Foxy’s Harbor Grille in St. Michaels, MD
We love the fact that this St. Michaels dock bar is known for its martinis. But besides that, Foxy’s has great food with an Island flavor (think jerk chicken, mango chutney, and fish tacos) along with a great selection of beers on tap. The restaurant is located on the dock of St. Michaels Marina, who generally have plenty of temporary slips available. But don’t say we didn’t warn you: have more than one martini and you might find it’s best to stay the night. Not a bad option, either. foxysstmichaels.com
The Cheshire Crab at
Pleasure Cove Marina, Pasadena, MD
The Cheshire Crab is a hidden gem, and we mean that literally. To reach it from the Bay, you have to head up Bodkin Creek and deep into Main Creek to Pleasure Cove Marina. The seafood is some of the best in Pasadena, but their burger is also memorable for non-seafoodies. Grab a bucket of beers (just $10) and head out to their deck to see one of the best views around. pleasurecovemarina.com/cheshirecrab
Thursday’s Steak and Crabhouse in Galesville, MD
Although the name of this dock bar is Thursday, we mainly go there early in the week for their all you can eat fried chicken, mussels, and steamed shrimp for less than $15. With 27 slips available for diners and a happy hour that lasts until 7 p.m., this is the place to be on gorgeous nights when you feel like getting out.