Top things to do

Gifts & Souvenirs in St Michaels & Tilghman Island

Preppy Redneck

Well of course they're friendly at the Preppy Redneck, where southern hospitality meets the maritime sensibilities of the Eastern Shore. Among all the pink, you'll find Scout tote bags, 'classy' red Solo drinking cu…
Pizza; Italian in St Michaels & Tilghman Island

Ava's Pizzeria & Wine Bar

From the dough to the mozzarella, it's all made in-house at this popular pizzeria where the pies are cooked in an 800°F oven. Serves 15 wines by the glass and offers a strong lineup of regional draft beers. It's usu…
Seafood in St Michaels & Tilghman Island

Crab Claw

The Crab Claw serves up tasty Maryland blue crabs to splendid views over the harbor. Avoid the Waterman's seafood sampler, unless you're a fan of deep-fried seafood. It's next door to the Chesapeake Bay Maritime Mus…
Museum in St Michaels & Tilghman Island

Chesapeake Bay Maritime Museum

Throughout its indoor-outdoor exhibits, the Chesapeake Bay Maritime Museum delves into the deep ties between Shore folk and America's largest estuary. Learn about a 19th-century lighthouse-keeper's life while explor…
Clothing in St Michaels & Tilghman Island

Chesapeake Bay Outfitters

More of a casual boutique than an outdoor apparel store, this welcoming shop will kit you out for a breezy day of sailing and adventuring in no time. And, yes, the store sells Sperry Topsiders, a preppy mainstay.
Bar in St Michaels & Tilghman Island

Carpenter Street Saloon

Get your grog on with the locals at this bar inside the oldest commercial building in town, built in 1887.
Historic Building in St Michaels & Tilghman Island

Cannonball House

This was the only house in St Michaels that was hit during the War of 1812. According to lore, a cannonball bounced off the chimney, barreled through a dormer window, rolled across the attic and then bounced down th…