Our Favorite Maryland Eastern Shore Restaurants

You’ll find plenty of delicious food and drink!

There’s something for every palate with an excellent selection of restaurants and bars close by. Listed below some of our favorite Maryland Eastern Shore Restaurants!

Trappe and Cambridge, MD Restaurants:

Trappe is a few minutes north of the B&B while Cambridge is 6 minutes south, just across the bridge. We have also included recommendations for Oxford and St. Michaels. All recommendations below are close to The Anchorage B&B. Click on the restaurant name to visit their website.

Momma Maria’s – Artisan pizzas or a variety of dishes that embody the bold tastes of Italy and Greece located in Trappe. Chef Michael Quattrucci has combined those classic Mediterranean flavors with local seasonal ingredients.

The Coffee Trappe – The Coffee Trappe in downtown Trappe offers home-cooked breakfast, lunch, daily specials, local and international coffee drinks & a variety of other refreshments. Their local coffee beans are roasted by Coastal Coffee Roasting in West Ocean City, MD.

Snappers Waterfront Cafe and Tiki Bar – Casual setting right on the water with a tiki bar island setting. Jamaican wings are a must! Rockfish wrap and Ruebens are good. Nice little tiki bar on the water and also has indoor seating. Some nights have live music.

Black Water Bakery – Great brunch/breakfast/lunch menu with healthy choices in a comfortable cafe setting. Also has a lot of pastries and home made bread and offer local coffee from the area.

Ava’s Pizzeria & Wine Bar – The food at Ava’s is excellent – they are known for their homemade meatballs. There are a lot of beer choices and wine on tap. It gets really busy on the weekends so would recommend going for lunch or early dinner.

Old Trappe Tavern, a family run place open 7 days a week serving classic lunch staples and modern favorites like rustic sandwiches, soups, and salads. For dinner, try their Eastern Shore-style dinner fare such as steak frites, pan-seared salmon with lump crab, and hand-formed crab cakes with classic cocktails, wine and beer. https://www.oldtrappetavern.com/

Carmela’s Cucina – A favorite local hang out run by a great Italian family. Good lunch place with slices of pizza or sandwiches. Dinners are good too with daily specials.

Rise Up Coffee Roasters – Locally brewed coffee, pastries, breakfast sandwiches and burritos.

Lil’ Bitta Bull BBQ – Great melt in your mouth brisket and barbecue, smoked locally. Large bar with several beer choices.

Suicide Bridge Restaurant – A great place for anyone who likes seafood. Has outdoor seating and is right on the water. Located 15 minutes beyond Cambridge in Hurlock.

Cambridge Drinks & Nightlife:

The Dive Club – A new destination of nautical escapism and delectable food and drink at a themed restaurant ⚓️ Classic tiki cocktails & shareable plates! You feel like you are on an old time ship. The portraits and items that decorate the walls have been donated by locals. Watch out for Chessie the Sea Monster!

RAR Brewing – RAR is a small brewery with craft IPA’s, wine, and a busy social scene. They offer a spacious tap room, a rotating beer menu, and a full food menu with smokehouse grub.

Blue Point Provision Company – Nice place to go for a drink and on the water. Seafood restaurant.

Vintage 414 – A great place to have a glass of wine or beer. Serves salads and yummy flatbread pizzas. Also has gourmet snacks and sells wine.

Blue Ruin – Blue Ruin Cocktail Bar and Restaurant has a speakeasy feel, with brick walls, a piano player, and “Small Plates with Intense Flavor”. With over 150 craft cocktails, wine, beer, and tapas size eats, it’s a fun place to visit!

Nearby Easton, Oxford and St. Michaels Dining:

North of the B&B are the communities of Easton and Oxford, both a little over 15 minutes from the B&B, and St. Michaels which is less than 25 minutes away.

Doc’s Sunset Grille – Located right on the Tred Avon River and facing West, Doc’s Sunset Grille in Oxford is an amazing place to be for sunset. A great place to eat and chill with some beers and watch the sunset during the summer months. Live music on the weekends. They offer rockfish wraps, one of the best crab cake sandwiches, and other light fare.

Capsize OXMD – Located in scenic Oxford, Maryland, Capsize serves American favorites on the calm waters of Town Creek. It’s a place locals like to frequent, where you can grab a drink and enjoy the waterfront dining experience. Seafood, salads, sandwiches. It’s also right next to the Scottish Creamery for great ice cream.

Hunters Tavern – Situated in the historic Tidewater Inn, Hunters’ Tavern brings relaxed fine dining and impeccable service to Easton. They offer award-winning happy hour specials, breakfast, lunch, dinner, and Sunday Brunch. The setting is nice during the summer with an outdoor patio and fireplace. There is also 2 bars inside and a more formal dining area.

Legal Assets Craft Food & Spirits – Offers an innovative menu with a reasonable price range. The ambiance is cozy and eclectic with outdoor seating (seasonal) that provides a beautiful shady patio. The bar atmosphere is also great, and many people come here for a nice dinner – it gets crowded so reservations suggested.

Out of the Fire – Great vibe with a seasonal menu open for both lunch and dinner located in downtown Easton. Menu includes specials with vegetarian options and the food is delicious!

Headwaters Seafood & Grille – Locally-owned seafood restaurant offering tastefully-made Eastern Shore classics. Great lunch or dinner spot with many seafood options as well as burgers, wraps, and daily specials.

Limoncello Restaurant and Wine Bar – In the historic town of St. Michaels with homemade pastas and a lovely Italian atmosphere with a friendly, courteous, attentive staff. Great food and one of our favorite places. Highly recommended.

Corah’s Corner – Great place to stop for lunch in St. Michaels. Fish and chips are outstanding! They sometimes have live music.

La Bodega – Small Latin American restaurant with fresh food and an upscale vibe. The menu is fabulous, and they offer a really good selection of beers from multiple different Latin American countries as well as excellent margaritas. Try their $6 tacos. Reservations recommended. https://www.rudefoodco.com/rude-bodega

Old Salty’s Restaurant – established in the 1980’s in a historic schoolhouse on Hoopers Island Rd in Fishing Creek, MD. With a distinct personality of being fit for a foodie, it’s also a great spot for locals and fun for the family. The fishermen are local and have been there for generations, fishing, crabbing, and harvesting oysters. Much of their seafood is sourced from the Chesapeake and local waters so you get the freshest seafood to your table. They also have delicious prime rib, Delmonico steaks, and other favorites.

Where Are the Oysters?

  • Suicide Bridge Restaurant – A gathering place for locals since the 1950’s! They offer lots of options: steamed, on the half shell, fried, barbecued and topped with crab imperial.
  • Headwaters Seafood & Grille – The seafood restaurant serves Fried Oysters on its appetizer, lunch, and dinner menus.
  • Hunters’ Tavern – The Tidewater Inn’s anchor restaurant offers an Oyster Po’ Boy on their lunch menu. Look for specials as well.
  • Legal Assets – Serving craft food and spirits in one of Easton’s beautiful tree-lined neighborhoods, Legal Assets bakes a seasonal Oyster Pot Pie.
  • Doc’s Sunset Grille – Dine on Fried Oysters while sitting on their deck right on the Tred Avon River.
  • Robert Morris Inn – Across the street from the Oxford-Bellevue Ferry, the historic 1710 Inn offers a variety of oyster choices including Chef Mark Salter’s Oyster Pot Pie.

What Our Guests are Saying: “Beautiful, unique and scrumptious hand-crafted breakfasts (locally sourced and in season) were spectacular! Pristine, comfortable, relaxing. Lots of activity options on site (kayaks, golf balls, painting, hammocks, croquet, bikes, huge private river front space). Woody and Michelle are lovely and do everything they can to make guests comfortable on site, and they recommend local spots to enjoy. Blue Ruin in Cambridge was a major highlight – we never would have found it if they hadn’t suggested it. The Anchorage 1800 is the perfect place to bring friends & family and make it a group trip weekend!” Diane