The Best Staycation in Every State

St. Michaels, Maryland

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ADDRESS
St Michaels, MD 21663, USA

Maryland’s Eastern Shore is an underrated treasure with the sparkling Chesapeake Bay as its gem. St. Michaels, where the history can be traced back to the 1600s, has oodles of Colonial charm. Still, there’s also plenty of modern shopping, top-quality dining, and activities like sailing or riding along on a skipjack, an oyster dredging boat specific to the Chesapeake—the H.M. Krentz offers group and private charters.

The Chesapeake Bay Maritime Museum is worth visiting to see its working shipyard and lighthouse dating back to 1879. Pop into the old sewing factory building to visit St. Michaels Winery’s tasting room, which produces wine from grapes grown in nearby Maryland vineyards. And while many crab restaurants close for the winter season, Chesapeake Landing Restaurant and Seafood Market is open year-round, selling raw seafood to cook at home and a full menu of items like crab cakes, stuffed and steamed shrimp, and fresh-caught rockfish. Or, pick up a pizza from Ava’s Pizzeria and Wine Bar.

 

Spend the night at the famous Inn at Perry Cabin, a luxurious historic retreat set on 25 waterfront acres with six of its own sailboats and yachts, plus a pool and spa. —Devorah Lev-Tov

The Berkshires, Massachusetts

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ADDRESS
The Berkshires, United States

In western Massachusetts' mountainous Berkshires region, the arts and the outdoors are vibrant no matter what time of year you visit.

 

Winter adventurers can choose from five ski resorts—including Berkshire East and Ski Butternut, where snow tubing parks supplement downhill slopes—then warm up their bodies and fire up their minds at MASS MoCA, one of the world's largest and most thought-provoking contemporary art museums.

 

Other seasons offer even more things to do in the Berkshires: gardens bloom to life in the spring; outdoor music, theater, and dance festivals pop up throughout the summer; and the Mohawk Trail's colorful fall foliage is an annual attraction for leaf peepers. Meanwhile, museums like The Clark Art Institute continually compete for visitors with new exhibitions, and Mount Greylock's scenic summit draws both Appalachian Trail hikers and gourmet diners year-round.

 

The abundance of activities is matched by an array of lodging options for all budgets, from campsites in state forests, to mountain-view cabins at the Wigwam Western Summit, to legendary inns and spas like Blantyre, Canyon Ranch, and Miraval. —Kim Knox Beckius