4 Romantic Fall Road Trip Ideas We Love

There's no better way to enjoy the autumn foliage than a road trip

Updated 09/28/17

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As the leaves start switching shades and temperatures finally dip down to sweater weather, there’s no better time to hop in the car and head off on a cross-country road trip where the drive is just as enticing as the destination. Pack your bags and set off to explore the great American outdoors cruising through some of the most scenic spots in the country, from the Blue Ridge Parkway in North Carolina to the Green Mountains of Vermont. It won’t be hard to convince your other half to join you on the drive, either.

Just mention a few key phrases (historic golf courses, fireside whisky and craft beer) and he’ll be planning the playlist before you know it.

Burlington, VT

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A five-and-a-half-hour drive from New York and a little less than three and a half hours from Boston, Burlington, VT, is just far enough away to count as a legit road trip while still being an easy drive for a quick weekend getaway. Call downtown Burlington’s charming Hotel Vermont your home-away-from-home as you cruise along the Scenic Route 100 Byway, dubbed “Vermont’s Main Street.” The 146-mile route weaves along the eastern edge of the Green Mountains through Stowe and Jefferson before winding back over to Burlington.

Pause along the way at Cold Hollow Cider Mill’s Apple Core Luncheonette for locally pressed cider (best paired with the spot’s infamous cider donuts, of course) or for a sweet treat from one of the state’s other claims to fame: the Ben & Jerry’s Factory. When you get back to the hotel, cozy up with a well-deserved craft brew selected by the nation’s first beer concierge and cuisine sourced from some of the local farms and bakeries you passed on your drive.

Asheville, NC

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Dubbed “America’s Favorite Highway,” the 469-mile Blue Ridge Parkway snakes through the highest elevations of the Southern Appalachians, running from The Great Smoky Mountains National Park in North Carolina to the Shenandoah National Park in Virginia. Along the way you’ll come across 382 overlooks and 91 historic buildings (Thomas Jefferson’s home of Monticello being one of them), but don’t think you have to drive the entire stretch to catch jaw-dropping views of the colorful fall foliage. Thanks to the varying elevations—and over 100 different species of trees—the Blue Ridge Mountains are known for one of the longest and most colorful leaf seasons, with vibrant forests that switch shades from mustard yellow to rust red.

From Asheville, take a day drip driving along U.S. Route 19 from Maggie Valley to Cherokee where you’ll find plenty of Instagram-worthy spots to snap pics of the changing leaves. Back in town, curl up with your other half in a hotel just as historic as the nearby sites: The Omni Grove Park Inn. Sure the vistas you saw along your drive were gorgeous, but nothing compares to the view of the Blue Ridge Mountains from the hotel’s Sunset Terrace, especially with one of Asheville’s notorious craft brews in hand.

Lenox, MA

Brian Bumby

Skip town and head to the Berkshires where you’ll be in the heart of New England’s fall foliage. Here, you and your significant other have plenty of options when it comes to soaking up the scenery. One of our top picks: the Mohawk Trail near Clarksburg, where you’ll have one of the best photo ops of the foliage at the infamous Hairpin Turn. If you’re after New England’s signature brick buildings, make your way through the charming college town of Williamstown before heading south on Route 7. While driving along the rolling hills, pause to pick apples and sample homebaked goods at streetside orchards and bakeries, creating your own moveable feast through the valley.

When you’re ready to call it a night, post up in Lenox, the “Switzerland of America, on the 220-acre Blantyre estate. Modeled after an ancestral home (aka castle) in Scotland, this English-inspired spot is about as charming as it gets, with private cottages showing off picture-perfect views of the meadow. The hotel will even pack a high tea-worthy spread for the road (complete with floral quilt and fine crystal) so you can picnic within prime views of the colorful peaks.

Bedford, PA

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Set your sights on the small town of Bedford, home to the annual Fall Foliage Festival. History buffs will love strolling around the town George Washington once marched through to squash the Whiskey Rebellion of 1794. Sleep in a Victorian bed and breakfast like The Chancellor’s House (which looks straight out of a movie set) and visit another one of the city’s historic sites: the 18-hole Old Course, one of the first golf courses in the country. When you’re ready to hit the road, head along Route 30, better known as the Lincoln Highway.

Cruise America’s oldest cross-country highway on the stretch from Irwin to Bedford, admiring the stunning fall scenery of the Allegheny Mountains. To really top off your stay in colonial America, warm up around the outdoor fire pit overlooking the Old Course’s 18th hole, or head to Frontier Tavern, housed in the 1806 Stone Inn building, and toast to the start of fall in the best way possible—with a round of Pennsylvania’s best artisanal brews.

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