Day Pass: Extend That Endless-Summer Glow With A Trip To St. Michaels

Now that your weekend agendas are starting to open up a bit, there's no better way to fill up some of that white space on your calendar than with a quick day trip to the coast. Our advice: Get outside the Beltway and head to one of our favorite destinations—St. Michaels, Maryland.
It’s a picturesque town (where the idyllic scenes in Wedding Crashers were filmed, no less) that highlights everything the Chesapeake Bay has to offer—all within just a few square miles. There’s plenty to do (and see, and eat, and buy) to make it well worth the two-hour drive from D.C. To prove it, we've put together an easy itinerary to help you make the most of these balmy end-of-summer days. All you need to do is hit the road!
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When you arrive, make a stop at the Chesapeake Bay Maritime Museum. We know there's plenty of history to explore in the District, but this place is so much more than a museum. You’ll find exhibits, demonstrations, boat rides on the Miles River, and a huge floating fleet of historic Chesapeake Bay watercrafts. The exhibits range from classic to quirky — our favorite new one is titled "Steamboats & Swimsuits."

Chesapeake Bay Maritime Museum, 213 North Talbot Street; St. Michaels; 410-745-4962.

Photo: Courtesy of Chesapeake Bay Maritime Museum
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St. Michaels Marina is a hub for this harbor town, but it's not just for boating types — even if you don’t have a yacht to dock, stop in for a cocktail by the pool or rent bikes to tour the town.

St. Michaels Marina, 305 Mulberry Street, St. Michaels; 800-678-8980.

Photo: Courtesy of St. Michaels Marina
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Want a tasty souvenir of your trip? Shop the Easton Farmers' Market for locally grown produce, artisan cheeses, decorative plants, crafts, and more. Between 10:30 a.m. and noon, you can catch some live music, too.

Easton Farmers' Market, Harrison Street Public Parking Lot, Easton; 410-822-0065. Open Saturdays from 8 a.m. to 1 p.m.

Photographed by Laura Miller
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Crabbing is big deal in the Chesapeake Bay area, and to experience the tradition for yourself, you'll want to meet Captain Russell Dize of Let's Go Crabbing. Russell is a sixth-generation Chesapeake Bay waterman who docks at Tilghman Island, just a short drive from St. Michaels. He'll take you out on the water, teach you to crab the way it's been done for hundreds of years, and you'll keep all that you catch — that is, if you can handle that much, um, crabbiness.

Visit Let's Go Crabbing for more information.

Photo: Courtesy of Let's Go Crabbing
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Enjoy breakfast, lunch, dinner, or afternoon tea at The Inn at Perry Cabin's restaurant, Sherwood’s Landing, and soak up the idyllic atmosphere of this low-key coastal oasis. It happens to be the only four-diamond restaurant on Maryland's Eastern Shore, and you can expect local fare prepared by a world-renowned chef, plus beautiful views of the Miles River.

The Inn at Perry Cabin, 308 Watkins Lane, St. Michaels; 410-745-2200.

Photo: Courtesy of The Inn at Perry Cabin
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For fresh seafood, frozen drinks, and (the essential) homemade crab cakes, check out Foxy’s Harbor Grille, a chill waterfront landmark with a Margaritaville-esque vibe.

Foxy's Harbor Grille, 125 Mulberry Street, St. Michaels; 410-745-4340.

Photo: Courtesy of Foxy's Harbor Grille
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Want a true worlds-away experience? Charter the Lady Patty yacht for a few hours or a full day. She sets sail daily from St. Michaels or Tilghman Island until the end of October. Reservations (and sunscreen!) are strongly recommended.

For information, reservations, and directions, call 800-979-3370 or reserve online.

Photo: Courtesy of Lady Patty Classic Yacht Charters
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St. Michaels is a mecca for antiques — after all, the town has been around for a few hundred years at this point. There are too many places to list, but we’ll start you off at The Gatz Home & Garden for a curated selection of one-of-a-kind finds.

The Gatz Home & Garden, 1007 Talbot Street, St. Michaels; 410-745-3700.

Photo: Courtesy of The Gatz Home & Garden
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Make the time for a detour to Tilghman Island, a true working watermen's village with excellent fishing and fresh seafood. It's also home to the last commercial sailing fleet in North America, the skipjacks, which are on display at Dogwood Harbor. While you’re there, rent kayaks or take a guided kayak excursion at Tilghman Island Marina.

Tilghman Island Marina, 6140 Mariners Court, Tilghman Island; 410-886-2500.

Photo: Courtesy of Tilghman Island Marina
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Grab a simple and delicious dinner at Ava’s Pizzeria & Wine Bar, which snagged the title of Best Pizza on the Eastern Shore. Our favorite? Conveniently, the Chef's Favorite — a white pizza topped with prosciutto, arugula, and a balsamic reduction.

Ava's Pizzeria & Wine Bar, 409 South Talbot Street, St. Michaels; 410-745-3081.

Photo: Courtesy of Ava's Pizzeria
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Take a tour of Eastern Shore Brewing, a production brewery located in the historic mill complex in St. Michaels. All craft beers are brewed on the premises, so don’t miss the tasting room – pick one of your favorites, or create a variety pack to take a little bit of St. Michaels home with you.

Eastern Shore Brewing, 605 South Talbot Street, St. Michaels; 410-745-8010.

Photo: Courtesy of Eastern Shore Brewing
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End your day in St. Michaels by settling in to watch a sunset over the Eastern bay, and relish in the fact that the only traffic jam nearby is a few boats angling for a spot at the dock.

Photo: Courtesy of St. Michaels Business Association

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