The 8 Best Leaf Peeping Towns in Vermont This Fall

Vermont transforms into a magical landscape each autumn as its famous maple trees turn brilliant shades of red, orange, and gold. For travelers seeking the perfect fall getaway, the Green Mountain State offers charming towns where nature’s color show takes center stage.

From mid-September through late October, visitors flock to these picturesque communities to witness one of nature’s most spectacular displays.

1. Stowe: Mountain Views and Classic New England Charm

Nestled at the foot of Vermont’s highest peak, Mount Mansfield, Stowe delivers postcard-perfect autumn scenery that attracts visitors from around the world. The town’s winding Mountain Road offers breathtaking vistas of the surrounding hillsides dressed in their fall finest.

Local tip: Take the Stowe Recreation Path, a 5.3-mile paved trail that winds alongside the West Branch River, for unobstructed mountain views without traffic. Peak foliage typically arrives in late September through early October, making it one of the earliest spots in the state to change.

After leaf peeping, warm up with a tour of the Ben & Jerry’s Factory in nearby Waterbury or sample authentic Austrian cuisine at the von Trapp Family Lodge, established by the famous family that inspired “The Sound of Music.”

2. Woodstock: Covered Bridges and Village Green Foliage

Often called America’s prettiest small town, Woodstock captivates fall visitors with its quintessential Vermont charm. Three historic covered bridges frame perfect foliage shots, while the meticulously maintained 19th-century buildings around the village green create a scene straight from a Norman Rockwell painting.

The nearby Marsh-Billings-Rockefeller National Historical Park offers hiking trails through managed forest land where conservation practices have created diverse tree species and spectacular fall color.

For the best panoramic views, drive up to the summit of Mount Tom or visit the nearby Quechee Gorge, known as Vermont’s Little Grand Canyon. Woodstock’s peak foliage usually occurs around the first or second week of October, coinciding perfectly with the town’s annual Harvest Weekend celebration at Billings Farm & Museum.

3. Manchester: Scenic Drives and Historic Inns

Surrounded by the Taconic Mountains and Green Mountain National Forest, Manchester offers some of southern Vermont’s most spectacular foliage viewing opportunities. The historic town center features impeccably preserved colonial-era architecture alongside upscale outlets and boutiques for those who want to mix shopping with their leaf peeping.

Manchester truly shines along its rural backroads. Route 7A between Manchester and Arlington provides stunning mountain backdrops against brilliant foliage. Hildene, the Lincoln family’s summer home, offers 412 acres of walking trails through colorful woodlands and gardens.

Fall travelers should aim for mid-to-late October to catch peak colors. After a day of exploration, unwind at one of Manchester’s historic inns like the Equinox Resort, which has hosted American presidents and literary figures since 1769.

4. Bennington: Autumn Colors in a Historic Setting

Revolutionary War history meets spectacular autumn scenery in Bennington, home to Vermont’s tallest monument. The 306-foot stone obelisk offers panoramic views of three states dressed in fall splendor for those willing to climb its 417 steps (or take the elevator).

Covered bridge enthusiasts will find paradise here, with three historic spans including the photogenic Paper Mill Bridge. The town’s location in Vermont’s southwest corner typically means foliage peaks slightly later than northern regions, usually mid-to-late October.

Art lovers can admire the extensive collection at the Bennington Museum, home to the largest public collection of Grandma Moses paintings in the world. After exploring downtown’s shops and cafes, follow the scenic Molly Stark Byway (Route 9) east toward Wilmington for 48 miles of spectacular foliage vistas through the Green Mountains.

5. Middlebury: Campus Beauty and Countryside Vistas

Home to prestigious Middlebury College, this charming town combines academic elegance with rural Vermont beauty. The college campus itself becomes a leaf peeper’s paradise in autumn, with its historic stone buildings providing perfect contrast to the fiery maples and golden oaks that line the grounds.

Venture just outside town to find Morgan Horse Farm, where these magnificent animals graze in pastures framed by colorful hillsides. The Middlebury Falls in the center of town creates a thundering backdrop as water cascades between buildings decorated with autumn foliage.

Foliage typically peaks during the first two weeks of October. Food enthusiasts should sample local specialties at the Middlebury Farmers Market or tour nearby Lincoln Peak Vineyard, where the grape harvest coincides with leaf season, offering wine tastings with spectacular views of the Champlain Valley’s colorful landscape.

6. Brattleboro: Artistic Vibe Surrounded by Hillsides

As Vermont’s artsy southern gateway, Brattleboro combines creative energy with spectacular natural beauty. The Connecticut River forms the town’s eastern border, with New Hampshire’s hills providing a backdrop to Vermont’s own colorful mountains. Downtown’s brick buildings and artistic flair create a unique setting for autumn exploration.

Wantastiquet Mountain offers moderate hiking trails and rewarding views of Brattleboro framed by fall colors. Being Vermont’s southernmost major town means Brattleboro’s foliage typically peaks later, usually mid-to-late October, extending the viewing season for travelers.

The town’s vibrant arts scene means visitors can enjoy gallery hopping between foliage drives. Don’t miss the famous Brattleboro Farmers’ Market, where local producers offer seasonal treats like apple cider donuts and maple products under a canopy of colorful trees at the peak of harvest season.

7. Montpelier: Smallest State Capital with Big Fall Views

Don’t let its size fool you. America’s smallest state capital packs tremendous autumn beauty into its compact footprint. The gold-domed Vermont State House creates a striking centerpiece against the backdrop of colorful hills that surround this charming city of just 8,000 residents.

Hubbard Park, located just behind the State House, offers 194 acres of trails through mature forests and a stone observation tower with panoramic views of the city and surrounding mountains in their autumn glory. The Winooski River winds through downtown, creating reflective surfaces that mirror the vibrant trees along its banks.

Peak foliage typically arrives in early October. Between color tours, visitors can enjoy Montpelier’s surprisingly sophisticated dining scene and numerous bookshops. The Vermont History Museum provides context for the landscapes, explaining how the state’s relationship with its forests has evolved over centuries.

8. Waitsfield: Mad River Valley Colors on Display

Tucked between the northernmost peaks of the Green Mountains, Waitsfield serves as the heart of the Mad River Valley, one of Vermont’s most spectacular foliage viewing regions. The combination of river valley, mountain slopes, and working farms creates a diverse landscape that explodes with color each autumn.

The scenic Route 100 corridor through Waitsfield offers countless photo opportunities, particularly at the iconic Warren Covered Bridge. For adventurous leaf peepers, Sugarbush Resort operates its Super Bravo chairlift during peak weekends, carrying visitors to 3,150 feet for breathtaking mountaintop views without the hiking effort.

Mid-to-late September typically brings the first color changes, with peak usually occurring around the first week of October. Time your visit to coincide with the Mad River Valley Craft Fair or Harvest Market for an authentic Vermont experience combining local artisans, farm-fresh food, and nature’s most brilliant display.