Destination: Bennington, Vermont

August 31, 2020

If a Vermont fall foliage road trip is on your bucket list, you are in good company. Thousands of visitors come to Vermont every fall to witness nature’s majestic transition from summer to winter.  Luckily, our tiny state has a full-time population of only 626,299, leaving ample space for us to welcome our leaf-peeping visitors.

Visitors to Bennington, Vermont come from all corners of the United States and across the globe to wander our winding back roads that are all aglow in foliage reds, yellows, and auburns.

Ask any innkeeper, museum docent or shopkeeper: the most common question raised is undoubtedly “when is peak foliage in Vermont?”  The fact is, that it varies from the north to the south. It also varies by elevation.

The perfect thing about making Bennington VT your foliage destination is that a short drive in any direction will surely reveal amazing colors.  And let’s face it, one of the coolest things to do during foliage is to wander the back roads and breathe in the beautiful color.

fall foliage leaf peeping old first church bennington vermont
Old First Church Bennington Vermont in fall foliage color. Photo Credit: Tara Schatz

Bennington is nestled in a valley carved out of the Green Mountains. With an elevation of only 815 feet above sea level, we tend to get our color later than the higher elevations. A ten-minute drive up the mountain to Woodford (elevation 2,165 ft) or fifteen-minute drive to Mount Equinox (3,855 ft) and the picture can change significantly. Likewise, color tends to change earlier in the north and make its way down to Southern Vermont. Any way you look at it, Bennington is situated perfectly to be your home base for your October foliage expedition.

bennington fall foliage vista red orange leaves
Bennington early fall foliage. Photo Credit Tara Schatz

Southern Vermont Fall Foliage Drives Near Bennington, Vermont

Whether you have an hour or a full day to explore the back roads of Southern Vermont, you’ll find a gorgeous fall foliage drive with your name on it. Here are some of the most popular back roads for leaf-peeping near Bennington, Vermont.

The Route 7A-Route 100 Loop

Manchester, Vermont during the fall. Photo Credit: Tara Schatz

Length of drive: 102 miles
Time to complete: 4-5 hours, with stops

  • Start your day in Bennington. We recommend fueling up on a great breakfast at a delicious Bennington diner or café first.
  • Head north on Route 7A, also known as the Shires of Vermont Byway.
  • Stop for fall foliage views and a short hike at Lake Shaftsbury State Park. The hike around Lake Shaftsbury is easy, and one of our top 5 fall-foliage hikes near Bennington.
  • Continue north through the town of Arlington and into Manchester. If you have time, visit Hildene, the former home of Robert Todd Lincoln. Hildene is a grand house with sprawling gardens, woodland trails, and a working farm.
  • Take Route 30 into the Green Mountains, past Bromley to Londonderry, Vermont.
  • In Londonderry, head south on Route 30, which coincides with Route 100 for a time.
  • Just before the town of Jamaica, you will see a sign for the federally-owned Ball Mountain Dam. This is a short detour with gorgeous views of Ball Mountain Lake and the surrounding mountains.
  • As you drive south on Route 100, you will head through several small towns including Jamaica, Wardsboro, and Dover. For more amazing foliage views, head to Mount Snow for a scenic chairlift ride.
  • In Wilmington, head west on Route 9 back to Bennington, where you can enjoy a relaxing dinner at one of our amazing restaurants, pubs, or breweries.

Kelly Stand Road to Grout Pond

Grout Pond in the Green Mountain National Forest. Photo Credit: Tara Schatz

Length of drive: 64.1 miles
Time to complete: 3-4 hours with stops

Kelly Stand Road is a dirt road that is not maintained in the winter. Because this route travels through the mountains, peak foliage happens a little earlier than the surrounding towns. You should start seeing great fall colors in early October.

Grout Pond is in the Green Mountain National Forest is one of the most spectacular spots for fall foliage photography. Although this loop is just under 65 miles, because you are on dirt and gravel most of the time, it will take 2-3 hours to complete.

  • Begin in Bennington and head north on Route 7.
  • Get off at exit 3 in Arlington and head west on Route 313.
  • Take a short detour to the Chiselville Covered Bridge, which is located on Sunderland Hill Road (see map above).
The Chiselville Covered Bridge in Arlington. Photo credit: Tara Schatz
  • Head back the way you came for a mile and turn left onto Old Mill Road, which turns into Kansas Road.
  • Turn right onto Kelly Stand Road.
  • Meander along this dirt road for roughly 11 miles. There are plenty of spots to stop and take in the scenery during your drive.
  • Turn right onto Grout Pond Road and park in the parking area.
  • Hike around Grout Pond, or just take in the views from the shore. The Pond Loop is an easy 2.6 miles, with great foliage views. If you have a canoe or kayak, there is a small boat launch right near the parking area.
  • Drive back the way you came, and turn left on National Forest Road 71.
  • Forest Road 71 continues for another 10 miles. If you have time, you can detour to Somerset Reservoir, which is another lovely lake surrounded by mountains.
  • Turn left on Route 9 to head back into Bennington.

Bennington, North Bennington, and Shaftsbury Fall Foliage Loop

Meyers Road, North Bennington, Vermont. Photo Credit: Tara Schatz

Length of drive: 20 miles
Time to complete: 1-2 hours with stops

This short loop includes three covered bridges, a historic mansion, and several beautiful back roads. This is a perfect fall road trip for visitors who don’t have a lot of time.

  • Begin in Old Bennington and take Silk Road to the Silk Road Covered Bridge. There is an area to park your car and explore the bridge.
  • Head to Route 67A and turn left.
  • Take a quick left onto Murphy Road to visit the Paper Mill Covered Bridge.
  • Continue on Murphy Road Turn to the Burt Henry Covered Bridge. There is a small picnic area and a park next to the Henry Covered Bridge.
  • Follow River Road and turn left on Park Street.
  • Turn left when you see the Park McCullough driveway and park in the parking area. Guided tours of the Park McCullough House are available on the weekends, and the gorgeous grounds and gardens are open year-round.
  • Follow the map above to loop from North Bennington to White Creek Road, Cross Hill Road, and Meyers Road.
  • Turn right on Route 7A to head back toward Bennington.
  • Visit the Robert Frost Stone House Museum on Route 7A in Shaftsbury. Tour the house and explore the grounds for more great foliage views.
  • Head back into Bennington for lunch or dinner.

More Back Road Fall Drives in Southern Vermont

Cattle grazing on a small farm in Southern Vermont during the fall foliage season. Photo credit: Tara Schatz

For even more adventuresome leaf-peeping drives around Bennington, click on the links below to go straight to the Google Map. Once you experience fall in Bennington, Vermont, you won’t want to go anywhere else!

  • Bennington/Pownal loop – This fall foliage drive takes you down some of the most lovely rural roads between Bennington and Pownal.
  • East Road to Route 313 and River Road, from Bennington to Arlington – This loop brings you through lots of farmland, over the West Arlington Covered Bridge, and alongside the Battenkill River before heading back to Bennington.
  • Bennington/Berkshires loop – This loop brings you south into the northern Berkshires, where you can drive to the top of the tallest peak in Massachusetts, visit a world-class art museum, and head north through the Green Mountains before landing back in Bennington.

Portions of the above rides are truly on the backroads, so please note to carry a paper map. The prettier the backroad, the more likely your GPS will misbehave.

Looking for a place to call home during your fall foliage vacation? Check out some of these great hotels, inns, and B&Bs in Bennington. Hope to see you this fall!