A Stroll Through Eastport
We like it this way…
BY: Erin Kopelman | PHOTOS: Lani Allen
Take a walk over the bridge from busy downtown Annapolis, bustling with Naval Academy midshipmen and the tourists that crowd City Dock, and you’ll find yourself in the peaceful yet lively neighborhood of Eastport, where locals welcome visitors who appreciate the slower pace.
Eastport is a picturesque residential neighborhood of historic bungalows and modern homes surrounded by marinas and boatyards and plenty of opportunities to dine dockside. And its small scale will allow you to keep walking and discover all of the locals’ beloved restaurants on foot. Come along on a stroll to some of our favorite spots.
Boatyard Bar & Grill: A Local Legend
The door to the Boatyard swings open almost constantly for good reason—the steady stream of guests is drawn in by the promise of well-executed favorites and a reputation that extends far beyond the local dock. At the heart of it all are legendary crab cakes that have developed a national following and a booming mail-order business. On a busy day, the kitchen turns out an astonishing volume while never compromising craft, a testament to their popularity and quality, as well as Chef Scott’s culinary lineage.
The menu features standout classics like a blackened mahi mahi sandwich, a seared tuna, and a smoked blue cat pâté that’s quietly become a favorite among those in the know. The Orange Crush remains the go-to refreshment. This is a place where consistency, energy, and local flavor come together in every dish.
Bread and Butter Kitchen: Morning by the Water
Perched on the water, Bread and Butter Kitchen is where everyone from sailors to families shows up for breakfast burritos and buttermilk biscuits.
Owner Monica Alvarado has built more than a restaurant; she’s built a movement. She champions local farms, and her commitment to food equity radiates through partnerships with community programs and nonprofits. On weekends, you will find a local musician tuning up on the deck, families settling in with scones the size of your fist, and friends splitting world-class vegan cheesesteak sandwiches.
Grab a table outside and watch the water traffic glide by while you sip iced coffee made with coffee ice cubes. (No diluted cold coffee drinks here!) You’ll start to understand why people in Eastport never seem to be in a hurry.
Forward Brewing: Local Beer, Big Personality
When Eastport neighbors Kelly and Camden realized their peninsula lacked a brewery, they decided to fix that. Forward Brewing is the result—and it’s as local as it gets.
Small-batch beers rotate constantly, with names that nod to nautical life and neighborhood lore. On a sunny day, the outdoor tables overflow with locals sipping citrusy IPAs or malty porters while kids play with chalk on the sidewalk. Their menu is compact but clever: soft pretzels with beer cheese, inventive flatbreads, and seasonal specials that lean into Maryland’s harvests.
Forward is a gathering place that reflects Eastport’s laid-back, roll-up-your-sleeves vibe. Stop in, raise a glass, and feel the current of community pull you in.
The Rest of the Roster
Leeward Market is the heart and soul of Eastport; it keeps breakfast casual with sandwiches where the locals have favorites and the staff remembers each of them. Eastport Kitchen leans classic and comforting with its delicious food made with local ingredients and offers a welcoming atmosphere where the owners and chefs chat with the guests and cook in an open kitchen. For white-tablecloth seafood, O’Leary’s is a longtime favorite, while Carroll’s Creek Café delivers sweeping water views, excellent food and service, one of the best happy hour deals in town, and a certified nut-free kitchen. For an original steakhouse, Lewnes is not to be missed with dark wood paneling and a small, carefully crafted menu of mouthwatering options. Arrive early to get a seat at Vin 909, the neighborhood darling for wood-fired pizza and an excellent wine list. For a beer and a story in a no-frills setting? Grab a stool at Davis’ Pub.
If you want to keep strolling while you have your snack, grab a drink from Oscar’s Coffee, a coffee food truck surrounded by folding chairs and string lights, and be sure to get a pastry from Cocoa & Pearl, a boat bakery. What could be more maritime than that?