Road Trips

The Ultimate New England Fall Road Trip

It's like a week-long scenic drive.
Portsmouth New Hampshire
Getty

You’ve seen the Instagram feeds. By late September, New England’s highways and byways explode with color and the region embraces its pumpkin-spiced, autumn-themed glory. It feels like all is right in the world. But where to begin?

Each of New England’s six states has its must-sees, but this itinerary heads north (sorry, Connecticut!) over a seven-day drive from Massachusetts’ Berkshire Mountains up through Vermont and New Hampshire, ending in Boston. Whether you’re an out-of-towner renting a car round-trip from Boston, or getting behind your own set of wheels out of NYC, we’re here to help you live your best fall life. Take this New England fall road trip for a test drive and let us know how we did.

  • Autumn foliage in the Berkshires region of Massachusetts
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    Day 1: Start in the Berkshires

    Start by dropping your bags at Tourists, a 48-room modern mountain hotel that opened in July on the banks of the Hoosic River in North Adams, Massachusetts. Before partaking in the on-site fun—this 55-acre site feels like endless summer camp for adults (read: new drinking buddies will be made)—you should stretch your legs. You can’t visit the Berkshires without a good power-walk or two—the hiking trails here promise a full dose of autumn. Make your way up Mount Greylock (pictured), the highest peak in the state (at 3,489 feet) or work your way down a stretch of the Appalachian Trail, which is just about a half-mile from the hotel. Considering you’ll be behind the wheel most the week, get those steps in now!

  • Daniel Silbert/Courtesy Copper Grouse

    Day 2: Drive from North Adams, MA to Manchester, VT

    Miles to go: 111

    From North Adams, hop on Route 2 to begin—and finish—the 63-mile Mohawk Trail through the Berkshire Mountains. It’s New England’s original scenic drive, and for sure Massachusetts’s most picturesque route come early October. As the name implies, the two-lane highway follows a Native American trade route, and it passes through 50,000 acres of parklands and forests (especially well-preserved around the Mohawk Trail State Forest, where bears and bobcats have been known to cross the trail). Nowadays, it’s also lined with slightly more modern trappings like art galleries, antique stores, cider stands, and cafes that are sure to pique your curiosity (read: drive slowly and prepare to stop—a lot).

    Head southeast toward Greenfield, then loop back around and go north to Vermont, where New England leaf peeping (yes, we hate this phrase, too) is at its finest. Here, in the Green Mountain State, expect more maple trees than anywhere else, meaning the brightest of yellows, oranges, and reds on nearly every highway and country road. Plan to reach Manchester Village by late afternoon. Check into Kimpton Taconic Hotel, and take full advantage of the much-deserved complimentary wine hour. Feast on American comfort food at farm-to-table restaurant the Copper Grouse (breakfast pictured, though we recommend the cheddar-stacked house burger with hand-cut fries for dinner).

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    Day 3: Drive from Manchester, VT to Stowe, VT

    Miles to go: 145

    Ditch the smartphone maps and venture down random streets off Highway 7A to create your own fall foliage adventure: Manchester’s surrounding Green Mountain National Forest does not disappoint. Later, restart the Google Maps and head to the summit of Equinox Mountain. You can only drive so far—to get to the tippity-top requires a short walk. Here, take in colorful panoramas that stretch from New York to New Hampshire. In the early afternoon, elevate fall road tripping to a new level with the Land Rover Experience Driving School back in Manchester. Choose from a one-hour off-road experience up to a six-hour obstacle-course challenge under the tutelage of an expert driver. Expect a few exhilarating (albeit sometimes nauseating) hours scaling muddy hills, braving huge ditches, and slipping and sliding through the Technicolor of the Green Mountains (pictured). Make sure you have a partner in crime to capture it all for social media. Leave late afternoon to arrive at Stowe Mountain Lodge in northern Vermont before sunset.

  • Jesse Schloff/Courtesy Stowe Mountain Lodge

    Day 4: Spend a day in the trees in Stowe, VT

    Miles to go: Zero. Time to chill TFO.

    Leave the car parked for the day to fully experience the outdoor fun at Stowe Mountain Lodge, which will be your home base again tonight. Road tripping and hiking seem boring compared to what’s on offer. Fly high above the fall foliage on one of the longest zip-lines in the country. Channel your inner Spider-Man or Tarzan with an aerial obstacle course, swinging through the Vermont treetops. Prepare to test your balance skills, jump between floating planks, climb and swing across ropes, and challenge yourself during this white-knuckled forest canopy experience. After, return to normal blood pressure at the spa and wellness center with the “Epic Mountain Mead,” a two-hour experience that includes a skin-nourishing milk and honey wrap and a 50-minute massage. Go into town for dinner at Plate, a small and stylish family-owned restaurant that’s the height of Vermont’s farm-to-table movement (even the veggie burger will impress hard-core carnivores).

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    Day 5: Drive from Stowe, VT to Mount Washington, NH

    Miles to go: 150

    Today is all about the scenic drives. Get an early start (with optimal lighting around 7 a.m.) for a joy ride between the mountain ridges of Stowe and Waterbury on the 14-mile Green Mountain Byway (a jazzed-up name for a highly scenic stretch of VT Route 100). Grab breakfast at Stowe Bee Bakery & Cafe and stock up on picnic supplies for later (including wine) at country store Stowe Mercantile. Then head southwest toward White Mountain National Forest (pictured), entering via Route 112. Soon, you’ll be on the Kancamagus Highway (or the “Kanc” as locals call it). Northern New Hampshire’s claim to fame is this highly scenic 35-mile stretch of Route 112, erupting with vibrant, changing leaves over multiple elevations. There are no gas stations, restaurants, hotels, and the like—nature takes center stage. Breathe in the fresh air and fill your Instagram feed with envy-inducing pics. Enjoy your picnic lunch at one of the route’s many waterfalls (map "Sabbaday Falls" or "Rocky Gorge"). Before sunset, drive to Mount Washington and unpack at history-steeped Glen House Hotel. This fabulous new-fashioned take on classic New England architecture is actually the fifth iteration of its c. 1851 namesake—it has burned down and been rebuilt four times previously (insert eye-popping, wow emoji here).

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    Day 6: Drive from Mount Washington, NH to Portsmouth, NH

    Miles to go: 115

    After a breakfast of maple syrup-saturated buttermilk pancakes and apple betty french toast at the Glen House, continue traveling back in time on Mount Washington Auto Road, considered America’s first manmade attraction—it dates to 1861. Don’t get it twisted: This is not a Disney ride. This mini-highway garnered “attraction” status as it was developed on private land (and originally as the Mount Washington Carriage Road). The road ascends through four ecological forest zones—from northern hardwood to boreal to krummholz/subalpine to alpine—up 4,618 feet from the base (umm, check your brakes beforehand). Expect plenty of lookout points along the way until you reach the highest summit in the Northeast: the top of Mount Washington at 6,288 feet. There’s a good chance of extreme cloud cover here, but wait it out. The weather is volatile and sunny skies could soon arrive. (Don’t believe us? Just ask the folks who work at the top at Mount Washington Observatory Weather Discovery Center.) In the afternoon, veer back onto public roads and go south toward the quaint coastal town of Portsmouth (pictured). Check into the cozy, inn-style Hotel Portsmouth, which screams Americana by design and is within walking distance to the town’s prolific craft breweries and awesome restaurants. Treat yourself to briny local oysters and the best hot lobster roll in all New England at Row 34 Portsmouth.

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