The Bennington Battle Monument during fall foliage season in Vermont
The Bennington Battle Monument during fall foliage season in Vermont. Photo credit: Tara Schatz

September 12, 2023

It’s hard to believe that fall is coming around again in Southern Vermont. It won’t be long before we’re trading our shorts for wool sweaters, munching on cider donuts, and taking in the jaw-dropping beauty that is the Vermont fall foliage season.

If you’re planning your Bennington fall foliage vacation, you’re in luck! We’ve compiled a comprehensive guide with all the very best things to do in Bennington this fall.

Read on to start planning a one-of-a-kind vacation that you can only have in Bennington, Vermont!

Take a Self-Guided Walking Tour in Old Bennington

The Old First Church and cemetery in Bennington, Vermont
The Old First Church in Old Bennington during the fall. Photo credit: Tara Schatz

While located entirely in the town of Bennington, a visit to Old Bennington, Vermont is a bit like stepping back in time. This historic village is home to fewer than 200 people, along with beautiful historic buildings, and a most colorful past. 

Whether you’ve explored Old Bennington before or are visiting for the first time, there’s a lot to discover on an Old Bennington walking tour. Our self-guided tour of Old Bennington will lead you past some of the area’s most interesting historic sites, including the Old First Church, the Bennington Battle Monument, and the site of the former Catamount Tavern.

Put on your walking shoes, park your car at the Bennington, Museum, and don’t forget your camera.

Celebrate the Harvest Season in Bennington

The bounty of harvest season provides lots of opportunities to enjoy the local flavors of fall while taking in those spectacular fall foliage views. Here are some ideas for enjoying farm-fresh food and celebrating the harvest in and around Bennington.

Find the Perfect Pumpkin for Pies and Jack o’ Lanterns

Pumpkins in a row at Armstrong Farm in Bennington VT
Armstrong Farm in Bennington, Vermont. Photo credit: Armstrong Farm

Bright orange pumpkins are a harbinger of fall, and there’s no better place to pick your favorites than at Armstrong Farm on Route 7 just south of downtown Bennington.

Not only is Armstrong Farm a great, family-operated pumpkin patch, but they also sell fresh veggies, pure maple syrup, gourds, jams, and honey! This is a unique destination that you won’t want to miss.

Go for a Vermont Fall Foliage Drive in Southern Vermont

A back road lined with colorful maple trees in Bennington VT
A back road lined with colorful maple trees in Bennington, Vermont. Photo credit: Tara Schatz

Make your home base in Bennington and embark on a few beautiful fall-foliage drives throughout Southern Vermont. We’ve compiled several fall foliage road trip options, lasting from a few hours to a full day.

Travel the back roads of Southern Vermont and the Northern Berkshires of Massachusetts to discover breathtaking views, unique museums and historic sites, and the small New England villages that make this area so special.

Get Outside in Bennington, Vermont

Fall foliage scene in Bennington, VT featuring the Bennington battle monument.
The Bennington Monument during fall foliage season in Vermont

Fall is one of the best times to enjoy the outdoors in and around Bennington, Vermont. Our parks, back roads, and waterways are alive with color and just begging to be explored. Here are some ideas for getting outside in Bennington.

Go for an Autumn Hike

Lace-up your hiking boots and enjoy the colors on the trees and leaves crunching beneath your feet. The Bennington area has some of the best hiking in Vermont, as well as the most spectacular views.

For starters, check out our 5 favorite trails in Bennington to hike during fall foliage.

Discover Bennington’s Covered Bridges

Henry Bridge North Bennington, VT
The Burt Henry Covered Bridge in North Bennington, VT

Bennington County is home to five beautiful covered bridges, and you’ll find three of them right here in the towns of Bennington and North Bennington. All of the Bennington covered bridges cross the Walloomsac River, and they are all within a mile of each other, so you can visit them all in a very short period of time.

Local tip: The Walloomsac River is a fabulous trout stream, and according to the Vermont Fish & Wildlife Department, much of it can be fished year-round. 

Here’s a brief overview of the three covered bridges in Bennington and North Bennington, Vermont:

  • Silk Covered Bridge – The Silk Covered Bridge crosses the Walloomsac on Silk Road, not far from its intersection with Route 67A in Bennington. This is a Town lattice truss bridge, built in 1840 and added to the National Register of Historic Places in 1973.
  • Paper Mill Village Bridge – The Paper Mill Village Bridge is another Town lattice truss bridge that carries Murphy Road across the Walloomsac River near its junction with Route 67A in Bennington. It was constructed in 1889 and added to the National Register of Historic Places in 1973.
  • Burt Henry Covered Bridge – The Henry Covered Bridge is located on River Road in North Bennington. Another Town lattice truss bridge, it was originally built in 1840 and rebuilt in 1989. The Henry Covered Bridge was added to the National Register of Historic Places in 1973.  There is a small parking and picnic area near the Henry Bridge. Be sure to visit North Bennington’s edible forest garden in McWaters Park, which is adjacent to the parking area. 

Attend a Local Outdoor Festival

Southern Vermont Homebrew Festival

Join the fun on Saturday afternoon, October 7th at the Southern Vermont Homebrew Festival. This popular fun, fall event is back celebrating homebrewers from around the region amidst the spectacular fall foliage. This is an outdoor event, rain or shine, and we recommend purchasing tickets in advance.

Downtown Bennington Harvest Festival

Join us for a fun day of activities, entertainment, delicious local food fare, and more in downtown Bennington, Vermont on Saturday, October 14th, 10am-4pm.

Tour a Historic Home

The Robert Frost Stone House Museum in Shaftsbury, VT
The Robert Frost Stone House Museum in Shaftsbury, VT

Get a taste of Bennington history during your fall vacation with a tour of one of our historic homes turned museums.

The beautiful Victorian-era Park McCullough House was built in 1864 – 1865 by attorney and entrepreneur, Trenor Park, and is considered one of the finest and best-preserved Victorian mansions in New England. You can visit this beauty, the working farm behind it, and the lovely, Mile-Around-the-Woods hiking trail all in one afternoon. Park McCullough House is located in the village of North Bennington and is open for tours on weekends until the end of the fall foliage season. Admission is $15 per person. 

For history on a smaller scale, check out the Robert Frost Stone House Museum on Route 7A in Shaftsbury, Vermont. This literary landmark was home to poet Robert Frost from 1920 – 1929,  which was a prolific time period of his writing career. He composed many of his most famous works here, including “Stopping by Woods on a Snowy Evening,” which was written on a hot June morning at his dining room table.  The Robert Frost House is open from Thursday – Monday, 10 am – 4 pm, until the end of October. 

Fall is one of the most beautiful seasons to explore the historic town of Bennington, Vermont. Whether you visit for an afternoon or a whole week, you’ll find plenty to do beyond leaf-peeping.