Embrace the Coziness of Fall in Vermont With This 3-Day Road Trip

Experience the glorious autumn colors and small towns of the Green Mountain State.

Country Road covered in orange leaves leading to a farm with colorful trees in the distance

September to October is one of the best periods to explore Vermont in the fall.

Photo by Youli Zhao/Shutterstock

One of the most exciting times to visit Vermont is during the fall, when yellow birches and red maples turn the Green Mountain State into a kaleidoscope of autumn colors. Venture into many of Vermont’s 251 towns and cities, and everything from the local breweries to the festivals move the season’s coziness level (the measure of a truly great fall destination) to an 11.

Up for an adventure for the harvest season? Try this three-day itinerary through Vermont in the fall. The trip starts in Burlington, mostly following I-89 and the mountains alongside the Scenic Route 100 byway before ending in Manchester. Along the way, the itinerary stops at Stowe and Woodstock, pairing the opportunity to see some of New England’s best fall foliage with some of the region’s most charming towns.

And while record rainfall flooded parts of Vermont throughout much of the past summer, the state has announced that most of the state’s stores, restaurants, and attractions are open to the public. Roadside shops and comfy Airbnbs are swinging back open for guests so Vermonters can show off their state.

Day 1: Burlington to Stowe

  • Approximate number of miles: 40

Starting in Vermont’s most populous city, the road trip starts in Burlington, a college town of eateries that will properly fuel you up for the trip ahead. (If you start the road trip on a Saturday, peruse the Burlington Farmers’ Market for apple-spiced treats and coffee.) Walk down the pedestrian-only Church Street Marketplace, where boutiques, cafés, and restaurants line the way alongside 19th-century buildings.

The leg from Burlington to Stowe is a particularly delicious one: Drive about seven miles south and tour the 1,400-acre Shelburne Farms, where you can watch cheesemakers turn the farm’s Brown Swiss cows’ fresh milk into Vermont cheddar. There’s the option of staying another night in Burlington and sampling some of the state’s breweries: Foam Brewers and Zero Gravity Brewery are among the best; City Brew Tours offers guided excursions.

Once in Stowe—no judgment if you stop by the Ben & Jerry’s Waterbury factory along the way—spend the night at one of Field Guide Lodge’s 30 rooms and suites. The indoor and outdoor fireplaces as well as the woodsy decor (think aspen tree wallpaper) add to the coziness of the fall trip.

>> Related: The Best Breweries to Visit in Vermont

Road leading into a forest, yellow trees surrounding the road.

Head down the Vermont’s Route 100 and admire the gorgeous scenery along the way.

Photo by Susan Natoli/Shutterstock

Day 2: Stowe to Woodstock

  • Approximate number of miles: 80

While Stowe is commonly associated with its white-capped peaks during the ski season, the town calls itself the “Color Capital” of autumn, so it’d be a shame not to explore the fall foliage the ski town has to offer. A 15-minute drive northwest of Stowe is Mount Mansfield, where travelers can gawk at the panoramic views from atop the highest point in the state. Smugglers’ Notch is another beautiful vantage point, located on Vermont’s Route 108—the narrow pass used to move supplies to and from Canada during the War of 1812. It’s now a road for sightseers, providing a canopy of yellow and orange leaves for drivers to admire.

After getting a fill of Vermont’s color-changing landscapes, drive down the meandering Scenic Route 100 Byway, and save time for pit stops at the Mad River Valley’s local craft shops, the River Glass Gallery, and natural sights like the 35-foot Moss Glen Falls. Once at Woodstock, settle in at the Woodstock Inn & Resort downtown, which comes complete with a golf course and saunas.

An early autumn foliage scene of houses in Woodstock, Vermont mountains

Woodstock, Vermont was established more than a decade before the United States.

Photo by Wirestock Creators/Shutterstock

Day 3: Woodstock to Manchester

  • Approximate number of miles: 60

Start your final day early so you have time to dive into Woodstock’s long history (which may or may not include a vampire). The town was founded before the United States got its independence, and several of its buildings are on the National Register of Historic Places, like Calvin Coolidge’s childhood home and the pink sandstone Norman Williams Public Library. But before exploring these points of interest, spend the morning walking around the Green—the town’s version of a Central Park–like space—and along the picturesque Middle Bridge, a charming structure framed by the distant mountainous landscape.

Once you’re ready, get back on Route 100 and head south to Manchester, a town of fewer than 5,000 people surrounded by the Taconic and Green mountains. And while the orange sugar maples and red oaks are memorable, there are more ways to celebrate fall in this town than foliage galore. AFAR writer Ashlea Halpern recommends pumpkin-picking and hay-riding at the Equinox Valley Nursery and fly-fishing in the Battenkill or Mettawee rivers.

Indulge in local fare at the farm-to-table Copper Grouse before ending the trip at the Big Green Barn. The owners of this 19th-century barn-turned-Airbnb converted the space into a photography studio more than 15 years ago. Now, guests interested in photography can get lessons from the hosts, who are also happy to organize a photo walk.

Chloe Arrojado is the associate editor of destinations at AFAR. She’s a big fan of cafés, dancing, and asking people on the street for restaurant recommendations.
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