Maryland's Chesapeake Bay offers quaint and memorable small towns, fresh-from-the-sea crab, and lots of laid-back leisure.
Written by: Heather Chadduck
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Discover Chesapeake Bay
You could spend a lifetime exploring the Chesapeake Bay, but even if you have only a few days and can't cover its 8,000-plus miles of coastline, a brief trip to Maryland's Eastern Shore will leave you with indelible impressions. You'll find everything from posh hotels to isolated B&B's, impromptu sailboat rides to luxury cruises, down-home crab boils to four-star cuisine.
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This artsy city hosts a plein air festival every July and is chockablock with art galleries, antiques shops, and restaurants. Don't miss the Saturday farmers' market in the square.
Sometimes called the Hamptons of the Chesapeake, Oxford is filled with many charming 300-year-old homes, some lining the Tred Avon River. Get there via the Oxford-Bellevue ferry, the oldest known privately owned ferry in operation in America.
Sometimes referred to as "the pearl of the Chesapeake," this laid-back town is home to annual regattas, lively music, and spectacular sunsets.
Where to stay: Osprey Point Inn, Restaurant, and Marina, 20786 Rock Hall Ave.; 410/639-2194 or ospreypoint.com.
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The most popular town on the Eastern Shore, St. Michaels has a beautiful harbor with several waterfront dining options, the Chesapeake Bay Maritime Museum, and Talbot Street, studded with more restaurants and boutiques, and a classic ice-cream shop.
Where to stay: The Inn at Perry Cabin, 308 Watkins Ln.; 866/278-9601 or perrycabin.com. Five Gables Inn & Spa, 209 N. Talbot St.; 410/745-0100 or fivegables.com.
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Scarcely populated, this tiny island makes for an ideal excursion if you want a nitty-gritty crabbing experience. Drum Point Market is open for lunch and dinner and is said to serve the best crab cake in the world.