Things To Do

Annapolis

Walk through downtown Annapolis, a great location for window shopping. Make sure to eat at one of the area's unique restaurants! At the end of Main Street, you will find the beautiful Annapolis Harbor.

Naval Academy

Visit the United States Naval Academy in Annapolis, MD! The academy grounds, known as "the yard," includes beautiful architecture and historical monuments.

Easton

Window shop on North Washington Street in Easton, home to many boutiques. Dine at "Out of the Fire" or "Scossa," two of Easton's favorite restaurants, or take a walk to the Hunter's Tavern located in the Tidewater Inn!

Ava's Pizzeria & Wine Bar

Ava’s was awarded “Best New Restaurant” and “Best Pizza” 3 years in a row by the readers of What’s Up Eastern Shore Magazine as well as “27 Points” for Food Quality from Zagat.

The Crab Claw

The business started in the 1950’s as The Eastern Shore Clam Company which was a clam and oyster shucking house. Local watermen came in daily with their catch of oysters, clams or crabs. In 1965, owners Bill and Sylvia Jones turned it into a restaurant called The Crab Claw which instantly became a St. Michaels Landmark. The Crab Claw Restaurant is still owned and operated by the same family to this day.

208 Talbot Restaurant

The mastermind behind the 208 Talbot kitchens is David Clark. Recently voted Best Chef on the Eastern Shore 2012 by the readers of what?s up Magazine, David is a 25+ year veteran of the industry. Together with property owner Paul Milne, 208 Talbot is a dining destination for both locals and visitors.

Theo's Steaks, Sides & Spirits

Theo’s Steaks, Sides and Spirits: a sleek, yet traditional steakhouse with hand carved steaks, upscale appetizers and all American classics.

Harbourside Grill

Located within St. Michael’s Harbour Inn, Marina and Spa. Overlooking the harbor and only 2 blocks from Talbot Street. Waterfront Dining at its best! Enjoy a meal prepared by the Best Chef Eastern Shore 2011 according to What’s Up? Magazine! Executive Chef David Hayes incorporates his English culinary background with local ingredients of the Eastern Shore.

Foxy's Harbor Grille

Still the best steamed seafood, homemade crabcakes, the best grilled burgers in town, yummy frozen drinks, and 15 incredible local revolving craft beers on tap…right on the harbor!

St. Michaels Winery

Lyon Distilling Company

Lyon Distilling Company is proud to be a micro, craft distillery on Maryland’s Eastern Shore. Dedicated to transforming raw ingredients into splendid liquor, step by step, in ultra small batches. Rum & Whiskey.

Eastern Shore Brewing

Great place for beer, with constantly rotating on tap options!

Shopping on Talbot Street

Stroll up and down talbot street to enjoy a variety of stores, boutiques, art galleries, and novelty shops.

Shore Pedal & Paddle

Shore pedal and paddle is your stop for kayak, paddle-board or bicycle rentals.

Patriot Cruises

Enjoy a sight seeing cruise or a cocktail cruise with Patriot Cruses. Leaving from the dock next to the Crab Claw, right outside the maritime museum's front entrance, these cruises are narrated and depart several times per day on the weekends. The boat has a climate controlled main deck with food and a full bar. See their website for more details. Its a great way to get out on the water and see the area from the water!

Chesapeake Bay Maritime Museum

The Chesapeake Bay Maritime Museum offers the nation's most complete collection of Chesapeake Bay artifacts, visual arts, books, and indigenous water craft.