Things To Do Recreation

Bennington and the surrounding area offer an abundance of opportunities for outdoor adventures. State parks, mountain lakes, swimming holes, and hikes for all ages and abilities abound. Bennington is nestled into the southwest corner of the Green Mountains and is a favorite stopping point along the Appalachian and Long Trails. For the casual walker there is no shortage of beautiful scenic walks with pastoral views and historic sites. The new Bennington Rail Trail beckons cyclists of all ages.

When temperatures drop, some of the best cross-country skiing and snow shoeing in the Northeast has brought the U.S. National Snowshoe competition to Prospect Mountain twice in the past five years.

There are several first-class alpine ski resorts within an hour’s drive of Bennington: Mount Snow, Bromley Mountain, Stratton Mountain, Jiminy Peak, and Berkshire East. Bennington is perfectly situated as a convenient and comfortable ‘base of operation’ for the entire southern Vermont/northern Berkshires area.

Breathtaking mountain views abound from every hole on our 18-hole championship golf course. For rainy day activities, Bennington has indoor golf simulator, a tennis bubble, and more.


This southwestern corner of Vermont offers offer a plethora of easily-accessible scenic hiking venues for all different ages and fitness levels. Ranging from easy country strolls to gnarly scrambles up steep mountains, visitors will find there are wonderful hiking opportunities for everyone.

Mile Around Woods

This scenic private preserve, adjacent to the historic Park McCullough House, is dedicated to conservation and agricultural uses. It offers a network of easy walking trails for ages 2-92 and is open to the public during daylight hours. Also known as ‘McCullough Woods’.

The Blue Trail at Bennington College

Bennington College’s beautiful bucolic campus is ideal for a relaxing country stroll. The Blue Trail, at the north end of the campus, connects to the McCullough Woods via the Aldrich trail. 

Greenberg Conservation Reserve

Off Route 7, just over a mile south of downtown Bennington is a 96-acre preserve consisting of beautiful meadows, wetlands and woods. The preserve features a network of easily accessed trails.

Robert Frost Trail from Lake Paran to the Robert Frost House

This is a fun two-mile trail that connects Lake Paran in North Bennington to the historic Robert Frost House Museum on Route 7A in Shaftsbury.

BATS Trails on Mt. Anthony

Bennington Area Trail System (BATS) developed and maintains a network of biking/hiking trails on Mt. Anthony in Bennington, VT. You can access the trails via the former SVC campus on Mansion Drive off Monument Avenue just south of Old Bennington. Park near the former gym. Check out the newest exciting trail with amazing views: Zaphod’s Run!

Click to view the Bennington County Recreation Map PDF
Two pups vs. the Appalachian trail. Woodford, Vermont, ten minutes from downtown Bennington.
Two pups take a break on the Appalachian trail. Woodford, Vermont, ten minutes from downtown Bennington.

Photo Credit: Tara Schatz

B.A.T.S Bennington Area Trail Systems

The trails start at the base of Mt. Anthony – visit website for details.

Downloadable trail maps, trail conditions and year long family friendly hiking and biking events. This volunteer run organization is also a great way for new residents to meet fellow outdoor-loving neighbors and get connected to the community. 

Green Mountain Club – Bennington Section

The Green Mountain Club Bennington Section includes a diverse group of members who are passionately interested in outdoor recreation and stewardship of the land. It welcomes anyone who is interested in hiking, walking, biking, snowshoeing, cross-country skiing, trail maintenance, and other outdoor activities.

Bennington is located in the beautiful Green Mountains and boasts access to the nearby Appalachian/Long Trail, as well as many other less well-known trails.

Please visit the website to learn more about opportunities for outdoor adventures around Bennington, VT.

Greenberg Headwaters Park

A few blocks from East Main Street in downtown Bennington, this preserve features a series of trails set in 168 acres of uplands, wetlands, and streams.

More trails near Bennington in the Green Mountain National Forest

Travel a few miles east of downtown Bennington heading up Route 9 into the Green Mountain National Forest and you’ll find any number of wilderness hiking trails. The best known of these trails is the Appalachian Trail—which is also the Vermont Long Trail in this part of the state. Park at the trailhead and give it a shot, heading north or south. Get ready to climb! 

There is a trailhead for Bald Mountain (aka White Rocks) right in town, off of North Branch Street Extension.

Town of Bennington Parks

Enjoy one of Bennington’s many well-maintained parks scattered throughout town.

Bennington Dog Park

Willow Park
Bennington, VT 05201

Looking for some socializing for your pup? Head over to the newly opened Bennington Dog Park at Willow Park (near the volleyball courts).

George Aiken Wildflower Trail

Bennington Museum
75 Main Street
Bennington, Vermont 05201

(802) 447-1571

Beautiful, interesting, and educational trail adjacent to the Bennington Museum.

State Parks

The Bennington area has many easily accessible State Parks with abundant hiking trails and beautiful lakes and rivers for fishing, swimming, and boating.

Lake Shaftsbury State Park

262 Shaftsbury State Park Rd
Shaftsbury, Vermont 05262

(802) 375-9978

A favorite local park offering a beach, swimming, boating, and easy hiking on a beautiful nature trail. Located on scenic Route 7A 12 miles north of Bennington.

Lake Paran, North Bennington

Houghton Lane
North Bennington, Vermont 05257

(802) 442-8457

Lake Paran is an undeveloped 35-acre lake that provides swimming, boating and fishing opportunities for the local community. There is a full service facility on the north end with a beach, lifeguarded swimming area and clubhouse.

Woodford State Park

142 State Park Road
Bennington, Vermont 05201

(802) 447-7169

Only 11 miles from downtown Bennington, Woodford State Park is like another world. Located at a significantly higher elevation than Bennington in the valley below, Woodford State Park offers cool breezes and a refreshing swim in summer and LOTS and LOTS of snow in winter. Beautiful scenery and campsites and a wonderful trail around the lake.

Emerald Lake State Park

65 Emerald Lake Lane
East Dorset, Vermont 05253

(802) 362-1655

This is a wonderful family friendly park for swimming and boating. Pack a picnic lunch and enjoy the water. Emerald Lake State Park is off of Route 7 in East Dorset, 32 miles north of Bennington.

Molly Stark State Park

705 Route 9 East
Wilmington, Vermont 05363


Enjoy this beautiful state park located on Route 9, 24 miles east Bennington. The park offers camping and a variety of hiking trails including one that leads to nearby Hogback mountain. Enjoy the views en route from the fire tower. 

recreation kayak bennington vermont
Down-time in Vermont. Lake Shaftsbury, ten minutes from downtown Bennington.

Photo Credit: Tara Schatz
Blue skies and Southern Vermont swimming holes.

Road Cycling and Mountain Biking

Bennington Bike Hub

160 Benmont Ave.
Bennington, Vermont 05201


The Bike Hub is a non-profit bike shop located in the former Highlander Bicycle shop.

Open Hours: Thurs-Sat 10am-6pm.

Bennington Area Trail System (BATS)

From BATS Facebook page: The Bennington Area Trail System (BATS) is located in the beautiful southwestern corner of Vermont. BATS was founded by a group of local bikers, runners, and hikers that advocate for multi-use singletrack trails for the enjoyment of area residents and visitors alike.

As a non-profit 501 (c)(3), BATS works with public and private landowners to plan, build, and maintain trails for sustainable, non-motorized use in and around the Bennington, Vermont area. BATS is a proud chapter of the Vermont Mountain Bike Association (VMBA), which helps support our chapter with grants and other resources that are important to our current and future success.

Ronnie’s Cycle

2601 West Road
Bennington, Vermont 05201

(802) 447-8606

Bennington Rail Trail

The new Bennington Rail Trail provides a bike and pedestrian friendly link between downtown Bennington and the Northside Drive area. The Bennington Rail Trail begins at the western end of the Walloomsac Pathway at the public parking area located on Depot Street.

Horseback Riding

Kimberly Farms

1214 Cross Hill Rd,
North Bennington, Vermont 05257

(802) 442-5454


Mt. Anthony Country Club

180 Country Club Dr,
Bennington, Vermont 05201

(802) 442-2617

Sunset Playland

Route 7A,
Bennington, Vermont 05201

(802) 442-3555

Family Fun Center featuring miniature golf, go-karts, and snack & dairy bar.

Tennis & Pickleball

Bennington Tennis Center

200 Lovers Ln,
Bennington, Vermont 05201

(802) 447-7557

The Mill Pickleball

160 Benmont Ave
Bennington, Vermont 05201

(802) 881-9141


Southern Vermont has some of the best downhill and cross country skiing on the East Coast

Prospect Mountain

204 Prospect Access Rd,
Woodford, Vermont 05201

(802) 442-2575

World class Nordic skiing right next door to Bennington at Prospect Mountain in Woodford

ski recreation near bennington vermont
It’s no wonder they call it The Sun Mountain. Bromey Mountain, 25 minutes from downtown Bennington, Vermont.

Photo Credit: Paul Orr


Spectator Sports

Southern Vermont Storm Football

Willow Park
Just off of Performance Drive
Bennington, Vermont 05201

NEFL North Atlantic Conference North Division Title holders. Home games held at Willow Park, Bennington, Vermont. Click link for season schedule and more information.

Back Road Ramblers

Request to have your Bennington tourism related business listing added, updated or deleted.


Plan your trip.