The Best Vermont Towns to Visit This Fall
September 07, 2023

Vermont’s fall foliage season is all about scenic drives, apple picking, hiking and exploring small towns. You can’t go wrong wherever you are in Vermont this time of year.

Here’s a list of some of the best Vermont towns to visit this fall foliage season, and where you’ll find easy access to the outdoors, memorable scenic drives and festive fall events.

-A rewarding view after a short hike up Owl’s Head in Groton State Forest.

Peacham and Groton

Once you’ve visited the town of Peacham for the first time, you’ll want to return every fall. The village center showcases historic New England homes, mountain views, a classic white steepled church and the Peacham Café.

To the south and west of Peacham is Groton State Forest, where you can find excellent hiking and paddling opportunities on 26,000 acres of state land spread out over several towns, including Peacham and Groton. Owl’s Head Mountain in Groton State Forest is an easy, rewarding hike—and perfect for kids—with gorgeous views from the top.

Event picks: Peacham Fall Foliage Day on Oct. 5, 2023 or Groton Fall Foliage Day on Oct. 7, 2023

Craftsbury and Greensboro

In the heart of Vermont’s Northeast Kingdom is the town of Craftsbury, home to the Craftsbury Outdoor Center, the Craftsbury (“The Genny”) General Store and Craftsbury Common.

Vermont foliage season typically gets a head start in the Northeast Kingdom compared to other parts of the state, but you’ll still be able to enjoy nice fall colors in Craftsbury in early October. Not far from Craftsbury is the town of Greensboro, where you’ll find Willey’s Store, the world-famous Hill Farmstead Brewery, and the Highland Center for the Arts.

Event picks: Footprints Trail Run in Craftsbury on Sept. 30, 2023 or The Vermont Philharmonic in Greensboro on Oct. 21, 2023

Subscribe to Happy Vermont

-Lefferts Pond in the town of Chittenden in Vermont’s Green Mountain National Forest. 

Chittenden

Chittenden is tucked away in the Green Mountain National Forest with many scenic locations, including the Chittenden Reservoir, Lefferts Pond and the Mountain Top Inn & Resort. Chittenden has a small population of about 1,230 residents. However, the size of the town is 74.2 square miles—or 46,000 acres—making it the largest town by area in Vermont.

The Green Mountains run along the entire eastern half of the town, creating a mood that feels secluded and wild, which is perfect for fall foliage viewing and outdoor exploration.

Event picks: The Killington Brewfest at nearby Pico Mountain on Sept. 30, 2023 or the Harvest Faire at Killington Resort on Oct. 7, 2023

Newbury

In the upper Connecticut River Valley is the town of Newbury. With a town green, historic homes, and the Newbury Village Store, Newbury is an ideal town to visit in the fall.

Head outdoors to Tucker Mountain Town Forest, which includes trails for hiking, horseback riding, mountain biking and more. The top of Tucker Mountain was cleared in 1808, creating a beautiful 360-degree view that’s hard to beat in the fall. (In early September 2023, the High Meadows trail from the upper kiosk to the summit will closed for a few weeks for erosion control work).

Event picks: The West Newbury Turkey Supper on Oct. 7, 2023, Groton Fall Foliage Day on Oct. 7, 2023, or the Cedar Circle Farm Pumpkin Festival in East Thetford on Oct. 8, 2023.

-A classic view of Stowe during Vermont fall foliage season.

Stowe

Stowe is a busy place during fall foliage season, and for good reason. Route 108—also known as the Notch—is a beautiful area for hiking and sight-seeing. The Notch is closed in the winter, and the road’s twists and turns make Route 108 an interesting drive through the mountains.

From the Notch, you can hike up to Sterling Pond or explore other trails. Stowe Pinnacle near Stowe Hollow is another popular hike that’s a favorite among locals. If you’re looking for an alternative to hiking, take a gondola ride at Stowe Mountain Resort to the top of Mount Mansfield, Vermont’s tallest peak. If strolling around town is your thing, Stowe’s Main Street is lined with shops, boutiques, cafes and restaurants.

Event pick: The Vermont Pumpkin Chuckin’ Festival in Stowe on Oct. 1, 2023, Indigenous People’s Day Rocks! in Stowe on Oct. 7, or the Stowe Foliage Arts Festival on Oct. 6-8, 2023.

Subscribe to Happy Vermont

-Route 100 near Vermont’s Mad River Valley.

Warren, Waitsfield and Fayston

Travel along Route 100 to the scenic Mad River Valley region. Warren is home to The Warren Store, The Pitcher Inn and Sugarbush Resort. Fall foliage season is perfect if you’re mountain biking at Blueberry Lake, hiking around Lincoln Gap, or taking a scenic chairlift ride at Sugarbush.

Mad River Glen in nearby Fayston also offers scenic chairlift rides, and the Appalachian Gap at the crest of Route 17 features gorgeous views and easy access to The Long Trail and Breadloaf Wilderness. In Waitsfield, visit shops and cafes on Bridge Street (where there is a one-lane covered bridge) or take a scenic drive along East Warren Road.

Event picks: SIPtember Fest at Mad River Glen on Sept. 16, 2023, Foliage Weekend at Mad River Glen on Sept. 23, 2023, or Community Day at Sugarbush Resort on Oct. 7, 2023.

-Reflective views on Lake Dunmore during Vermont’s foliage season.

Ripton, Goshen, Salisbury

This part of Vermont is home to the 16,000-acre Moosalamoo National Recreation Area. It includes more than 70 miles of trails for hiking, biking, camping, and fishing. In Goshen, head over to the Blueberry Hill Outdoor Center (next to the Blueberry Hill Inn) for hiking, mountain biking, and trail running.

In Ripton, stop by the Ripton Country Store or drive along Route 125, which is also known as Middlebury Gap. For mountain views, head over to Lake Dunmore in Salisbury, or take a hike up to Silver Lake.

Event picks: Bristol Harvest Festival on Sept. 23, 2023 or the Middlebury Car Show & Fall Festival on Oct. 15, 2023.

Montgomery and Jay

Montgomery in northwestern Vermont is known for its six historic covered bridges. This small town is in Franklin County, an area of Vermont known for dairy farming. But Montgomery, located not far from Jay Peak Resort, has a mountain-town feel.

A few miles from Montgomery’s Main Street is Hazen’s Notch, a scenic, dirt road mountain pass.  About 10 miles of the Hazen’s Notch trail network are open for walking and hiking in the summer and fall. These trails are located at the High Ponds Farm, a privately owned nature preserve located in the Hazen’s Notch Area of Montgomery.

You can also try hiking at Jay Peak or take a drive on Route 242, one of the most scenic drives in Vermont.

Event picks: Ecstatic Dance Party at the Montgomery Center for the Arts on Sept. 23, 2023 to ring in the Fall Equinox or the Bean and Brew Festival at Jay Peak on Oct. 14, 2023.

-Fall foliage season in Woodstock does not disappoint.

Woodstock and Quechee

Woodstock is another popular town that lives up to the hype, especially in the fall. Stop by the historic Billings Farm & Museum, explore the Marsh-Billings-Rockefeller National Historic Park, or hike up Mount Tom for scenic views. Stroll through downtown Woodstock and visit the The Yankee Bookshop or the F.H. Gillingham and Sons general store. Grab a cocktail at Au Comptoir and plan on dinner at The Prince and The Pauper restaurant or the Woodstock Inn & Resort.

A few miles away in nearby Quechee are Simon Pearce, the Vermont Institute for Natural Science, and Quechee Gorge.

Event picks: Woodstock Apples and Craft Fair and Food Truck Festival on Oct. 7-8, 2023 or Norwich Barns and Farm Tour on Oct. 14, 2023.

-A view of Mount Snow’s ski trails from East Dover in early fall.

Wilmington and Dover

Near the Vermont-Massachusetts border is one of the most scenic regions of Vermont—the Deerfield Valley. Wilmington and Dover are at the heart of the area, and visiting foliage season is a perfect time to visit.

Main Street in Wilmington—the intersection of Routes 100 and 9—includes locally-owned shops, cafes and restaurants. Try Bartleby’s Books, Dot’s of Vermont restaurant,  Alpenglow Alpine Bistro and Sticky Fingers Bakery.

Take a hike in the Dover Town Forest or soak up the foliage as far as the eye can see at the 100-mile view at Hogback Mountain. Mount Snow, located in West Dover, hosts events, scenic chairlift rides and outdoor recreation opportunities.

Event picks: the Wine and Harvest Festival in Wilmington and Mount Snow on Sept. 22-24, 2023 or the Mount Snow Oktoberfest on Oct. 7, 2023.

Manchester and Peru

In southern Vermont, the town of Manchester and the surrounding area are a must-see during fall foliage season.

Manchester is home to the Northshire Bookstore, Equinox Valley Nursery and Hildene – The Lincoln Family Home. Some of the best places in Manchester can be found outdoors at places like Equinox Pond and the Equinox Preserve, a protected area near the base of Mount Equinox with 11 miles of trails for walking, hiking, and mountain biking.

Prospect Rock is another gorgeous hike with views of Manchester and the Taconic Mountains. If you’re up for a steep and scenic mountain drive with panoramic views at the summit, head up to Mount Equinox Skyline Drive.

In nearby Peru, stop by Hapgood Pond in Peru, which is located on U.S. Forest Service land and is a nice spot to soak up the fall colors. Peru is also where you’ll find Bromley Mountain, J.J. Hapgood General Store, Main Street Makery, Bromley Market, and Seesaw’s Lodge.

Event picks: The Peru Fair on Sept. 23, 2023 or the Southern Vermont HomeBrew Festival in Bennington on Oct. 7, 2023.

-A sugar maple tree during Vermont’s fall foliage season.

Happy Vermont Podcast

In this 2020 podcast episode, “The Prettiest Vermont Towns to Visit During Fall Foliage,” I highlight additional best towns to visit in Vermont fall foliage season, as well as places to explore along the way. You can find my podcast on Apple Podcasts, Spotify, Amazon Music, Google Podcasts and iHeartRadio.

If you’re looking for suggestions on the best Vermont towns to visit in fall, please get in touch. You can send me an email at [email protected].