Fall Weekend Getaway Ideas

Getaway from: Washington, D.C.

This traditional country road cuts a ribbon through small-town life in Virginia’s hilly southwest. Fall weekends call for fresh cider from a red-roofed log-cabin store, bluegrass concerts, and spectacular views at every turn in the road.

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Getaway from: Boston, New York City

Forgotten vestiges of the past—from furniture and bric-a-brac to take-a-load-off roadside cafes—are rediscovered and given a modern dust-off in the Berkshires. This four-season destination is especially breathtaking in fall, when forest canopies are brilliant shades of red and gold. Among the winding, leaf-strewn roads, you’ll want to pull over at the pleasantly rustic Old Inn on the Green, where dinner is lit entirely by candles.

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Getaway from: Portland, Seattle

In this Oregonian sport mecca, the mighty Deschutes River and trout-filled mountain lakes mean plenty of action on the water. Spend your days whitewater rafting or fly-fishing (or, if you’re a lubber, stick to the hiking trails in nearby Deschutes National Forest), and, come evening, cap it off with a glass of fantastic Washington wine.

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Getaway from: Chicago

At the northwestern tip of Illinois, the town of Galena counts fewer than 5,000 residents, but draws more than a million visitors each year. The appeal? A great Main Street, trolley tours past beautiful 19th-century buildings, canoeing trips along the Galena River, and, for history buffs, seeing the place where President Ulysses S. Grant’s family lived and worked—and where he himself lived for about two years. The town also has galleries, craft shops, and boutiques.

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Getaway from: Boston, New York City

This town, filled with Victorian and Federal-style homes, is the perfect spot for a low-key romantic getaway. Expect antique stores, wine shops, and moderate biking and walking trails, set along the eastern shore of the Delaware River. For the utmost in romance, take a horse-drawn carriage ride through the historic part of town.

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Getaway from: San Francisco

In Northern California’s Mendocino County, the 25-mile-long Anderson Valley encompasses several tiny communities. In one such town, the folks at the Philo Apple Farm (who once owned French Laundry) grow 80 varieties of apples and rent out charming cottages. The vibe is very low-key, and there’s not a lot of infrastructure, so the area’s wineries are best explored by car. Be sure to sample the specialty, pinot noir.

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Getaway from: Washington, D.C.

The warm mineral waters of Berkeley Springs have long been touted for their healing properties. The surrounding area is also perfect for hiking and birding. Case in point: Berkeley Springs State Park, where you can sample treatments at the historic spa and also spot cardinals and bluebirds.

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Getaway from: Denver

A renowned art colony for more than 100 years, Taos abounds with museums and galleries. It’s a walk-able town, where desert pine trees cast sparse shade over adobe buildings, at the foothills of the Sangre de Cristo Mountains. You’ll find that lots of the art reflects the surrounding southwestern landscape—how could it not?

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Getaway from: Boston

In leaf-peeping season, it’s all about the views—and hiking, fishing, and simply exploring on foot—in this scenic New Hampshire town and its surroundings. Drive Route 10, between Keene and Walpole, to discover four historic covered bridges (also known as “kissing bridges”) and 3,165-foot Mount Monadnock, which has views all the way to Boston.

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Getaway from: Chicago

Best known as the home of the University of Notre Dame, South Bend scores high for college-football enthusiasts. If you can tear yourself away from the football stadium—and the institutions that house game memorabilia—there’s also an array of outdoor activities such as whitewater rafting and hiking through nature preserves.

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Getaway from: Washington, D.C.

Virginia’s Shenandoah National Park is lovely, easily accessible, and kid-friendly. Road trip along the scenic and slow Skyline Drive, stopping for family photos above vast landscapes of America’s oldest mountains, brilliant red and gold in the fall. Big Meadows lodge has rustic wood-paneled rooms and a playground for kids.

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Getaway from: New York City

New York’s Finger Lakes have gorgeous scenery—plus the wines to toast them with. The area has more than 35 wineries on the Seneca Lake Wine Trail, all sited along routes 14 and 414 in a loop around Seneca Lake. Check into a romantic Victorian B&B, then start your tour with the dry Rieslings at Wagner Vineyards.

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Getaway from: Seattle

Set in the Cascades, the wintertime ski trails at Snoqualmie Pass are a mountain-biker’s dream in warmer weather. Bordered by national forest preserve, the area offers an array of great beginner to advance-level trails that also happen to be among the state’s best places to spy fall foliage. The payoff is indisputable: Several the more challenging lead to views of Mount Rainier.

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Getaway from: Chicago

Ditch your car and catch a ferry from Michigan’s Mackinaw City or St. Ignace, and 15 minutes to reach the shore of the 2,000-acre Mackinac Island. Horse-drawn taxis greet you at the dock at this former summer colony (the British built a fort here in 1780) on Lake Huron, where you’ll travel back in time to the turn of the century. Live like a local, exploring by bike and dining on fresh seafood come sunset.

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Getaway from: Boston

Acadia National Park’s Mount Desert Island is the largest island off the coast of Maine. A reliable bus network stops throughout the park, but it’s the perfect cycling and kayaking destination. In fall, the tourist crowds dissipate, it’s blissfully quiet, and you can tuck in seasonal dishes like slow-braised ribs with maple glaze by the fireplace at Red Sky restaurant.

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Getaway from: Denver

Colorado Springs—the state’s second largest city—is perfect for a sybaritic retreat. With a sumptuous resort and proximity to artsy Manitou Springs (which has long drawn travelers to its mineral waters), the metropolis is one of the most well rounded in an area historically marked by mining and ranching. Weave hiking, spa treatments, shopping, and hearty seasonal fare into one indulgent long weekend.

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Getaway from: Washington, D.C.

Central Pennsylvania’s Amish communities provide a glimpse of a simpler time. Driving from town to town is easy, and ideal in the fall when leaf peeping is at its peak (buggy rides are another way to go). Snack on homemade shoofly pie while shopping for souvenirs at the Bird-in-Hand farmer’s market and enjoy dinner at a historic B&B’s wine cellar.

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Getaway from: Seattle

Washington’s premier wine destination is polished—with cafés and galleries clustered in a historic downtown—but not pretentious. Its Native American-derived name means “many waters,” but today wine is the only liquid that flows abundantly in this dry landscape. Sip cabernet sauvignon and merlot on half- or full-day vineyard-hopping tours in fall harvest season.

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