Fall is a fabulous time to get outside with your family for some great hiking in Bennington, Vermont. The heat of summer is dissipating, along with those pesky mosquitoes, and you’ll discover crisp, clear days, beautiful fall foliage, and maybe even some wildlife. 

The following Bennington hiking trails are perfect for family outings, fall photography, or just meandering in the woods. 

Lake Shaftsbury State Park, Shaftsbury

A fall foliage scene at Lake Shaftsbury State Park. Photo credit: Tara Schatz
Lake Shaftsbury, Vermont in autumn. Photo credit: Tara Schatz

This 84-acre park is small but well-loved by locals and tourists alike. It is most popular as a picnic and swimming spot for local families, but the trail around the lake is underappreciated and quite lovely, especially in autumn. Lake Shaftsbury State Park is 11 miles north of Bennington on route 7A. 

The hike around Lake Shaftsbury is more of a ramble — a mile in length, meandering through the woods, then wetlands, then back into the woods, with a constant view of the lake. Be on the lookout for a variety of birds — waterfowl are plentiful most of the year, and bald eagles and osprey have been spotted on numerous occasions. 

Lake Shaftsbury State Park is open from Memorial Day weekend to Indigenous People’s Day from 10 am to sunset. You can visit the park in the offseason or in the early morning by parking outside the gate.

After your hike, drive south on Route 7A for another mile and visit the Chocolate Barn for the best ice cream you’re ever likely to taste in Southern Vermont. For more on this hike, check out An Autumn Walk Around Lake Shaftsbury on Back Road Ramblers or download a trail map and guide. 

Difficulty level: easy

Length of trail: 1-mile loop

Kid appeal: swimming, a boardwalk through wetlands, decent fishing, boat rentals

Dogs: on leash

Fee: $4 for adults, $2 for children. 

Greenberg Headwaters Park, Bennington

The Greenberg Headwaters Park is a 168-acre gem within walking distance from downtown Bennington. Numerous hiking trails criss-cross the property, taking you from a beautiful upland meadow, through hardwood forests, and along the Walloomsac River. Wildlife is abundant throughout the year, so be on the lookout for otter, beaver, muskrat, turtles, and the resident barred owls. 

You can access Greenberg Headwaters Park from three parking areas on Beech Street, Belvedere Street, and Morgan Street in downtown Bennington. There is a short boardwalk and wetland viewing platform near the Morgan Street entrance, but if you want to hike, park at the Beech Street or Belvedere Street parking areas.

Difficulty level: easy

Length of trail: varies

Kid appeal: stream play, wildlife, footbridge

Dogs: yes

Fees: none

Woodford State Park, Woodford

Fall foliage surrounding Adams Reservoir in Woodford State Park, Vermont.
Fall foliage in Woodford State Park, Vermont. Photo credit: Tara Schatz

The hiking trail in Woodford State Park brings you around Adams Reservoir, a gorgeous, tree-lined lake nestled in the green mountains about 11 miles from Bennington. Because Woodford State Park is in the mountains, you’ll find that it’s much cooler here than in Bennington. Definitely pack a sweater or jacket for fall hiking. 

The trail around Adams Reservoir is dark and mossy, traveling through thick stands of hemlock and spruce, with great views for much of the hike. There are several easy stream crossings, and you may even see the carnivorous sundew plants if you look very carefully along the shore.

Woodford State Park is open from Memorial Day weekend until Indigenous People’s Day. You can visit in the off-season, but you have to park your car outside the gate and walk-in. Download a trail map from Vermont State Parks. 

Difficulty level: easy to moderate

Length of trail: 2.7-mile loop

Kid appeal: swimming, playground, boat rentals

Dogs: on leash

Fees: $4 for adults, $2 for kids

Mile Around Woods, North Bennington

The Mile Around Woods trail sits behind the beautiful Park McCullough house in North Bennington. This loop starts by taking hikers through beautiful farm fields of grazing horses, then meanders through a hardwood forest on a lovely, wide path. The forest loop is exactly a mile long, but you can make the adventure last by traipsing across several fields, or by visiting the historic Park McCullough House and Hiland Hall gardens.

Park McCullough House is open for tours on Friday, Saturday, and Sunday from May to October.,The Hiland Hall gardens have been meticulously restored and are located behind the main house. For an overview of the trails, please visit the Fund for North Bennington.

Difficulty: Easy for all ages

Length: 1-mile loop with options for longer hikes

Kid appeal: farm animals, wildflowers, rocks for climbing

Dogs: on leash

Fees: None, unless you want a tour of the historic house

Harmon Hill on the Appalachian Trail, Bennington

A fall foliage scene of a footbridge over a river in Bennington, Vermont on the Appalachian Trail.
The Appalachian / Long Trail in Bennington, Vermont. Photo credit: Tara Schatz

Choose a dry day to hike Harmon Hill on the Appalachian Trail/Long Trail, which is located on Route 9 just east of Bennington. Park your car at the Appalachian Trail parking area on the north side of the road, and cross Route 9 to head south.

This is a 3.6-mile out-and-back trail with a total elevation gain of 970 feet. It’s very steep at the beginning, with lots of rocks and switchbacks. The trail levels out after about a mile, traveling through a lovely meadow and ending with gorgeous views of Bennington, Mount Anthony, and the Taconic Range. The top of Harmon Hill is a great spot for an autumn picnic. Read a detailed overview of the trail and download a trail map from the National Forest Service.

Difficulty: moderate to strenuous

Length: 3.6-miles round trip

Kid appeal: Rock scrambles

Dogs: Yes

Fees: None

There’s nothing like a woodland hike to get you excited about fall in Vermont. After your workout, indulge in a well-deserved meal at one of our many Bennington restaurants.