Bennington Area Hikes

Let’s HikeVT! We’re featuring the Bennington area with easy, moderate, and difficult trails that take you to backcountry ponds and panoramic views of Southern Vermont. The accessible trail is in Lake Shaftsbury State Park, just north of Bennington.

Little Pond Trail – EASY
Harmon Hill – MODERATE
Bald Mountain – DIFFICULT
Shaftsbury State Park – EASY, ACCESSIBLE

From Little Pond Road parking lot:

Little Pond Trail – EASY

» 5 mi round trip, approx. 200 ft elevation gain

Starting from a small parking lot on Rt 9, the trail follows a dirt road past a few houses to a power line that provides nice views. From there, it continues as a flat woods road walk to Little Pond.

Driving directions to Little Pond Parking Lot Route 9

From Bennington: Head east on VT-9 E. Pass through the village of Woodford. 1.8 mi after passing the Woodford Mountain General Store, the Little Pond parking lot will be on your left. The dirt lot has a wooden trail sign in it.

From Wilmington: Head west on VT-9 W. 1.4 mi after passing the entrance to Woodford State Park, the Little Pond Parking lot will be on your right. The dirt lot has a wooden trail sign in it.

Via Public Transit: The Green Mountain Community Network‘s Emerald Line connects Bennington and Wilmington, passing the Little Pond Trailhead. For more information, including current operating schedule, call 802-447-0477 and visit https://www.greenmtncn.org/emerald-line.html.

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From Long Trail/Appalachian Trail parking lot:

Harmon Hill via the Long Trail – MODERATE

» 3.6 mi round trip, approx. 1265 ft elevation gain

Following the Long Trail south from Route 9, a steep rock staircase provides a thigh-burning hike to the top of the ridge. From there, you will be relieved to find mostly level terrain to the summit where you will find wide views of Bennington and the Taconic Ridge.

Driving directions to Forest City parking lots on Camel’s Hump Road in Huntington:

From Bennington: Head east on VT-9 E. 1.5 mi after passing Woodford Hollow Elementary School, the large parking lot will be on your left, marked by a roadway “P” sign. If you see a brown “Green Mountain National Forest” sign and a yellow pedestrian crossing sign, you have just missed it.

From Wilmington: Head west on VT-9 W. 2.6 mi after passing the Woodford Mountain General Store, the large parking lot will be on your right, just after a large brown “Green Mountain National Forest sign and a yellow pedestrian crossing sign.

Via Public Transit: The Green Mountain Community Network’s Emeral Line stops at the LT/AT Trailhead parking lot on its route between Bennington and Wilmington. For more information, including current operating schedule, call 802-447-0477 and visit https://www.greenmtncn.org/emerald-line.html. They also run a call-ahead trailhead service to/from Bennington. Info at: https://www.greenmtncn.org/transportation.html.

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From Bald Mountain/White Rocks Parking Lot:

Bald Mountain – DIFFICULT

» 8.2 mi round trip, approx. 2100 ft elevation gain

This blue-blazed trail follows an old woods road under the highway then gradually becomes a footpath. After about 3 miles, a spur trail leads to White Rocks with excellent views of Bennington. From there, continue to the junction with West Ridge Trail and turn left to reach the summit in 0.1 miles.

Driving directions to Bald Mountain/White Rocks parking lot in Bennington:

From Bennington: This trailhead is right in Bennington. The parking area is at 449 North Branch St.

From Wilmington: Take VT-9 W to Bennington. Once you enter the town, turn right on Branch St. In .3 mi turn right on North Branch St. The parking area is at 449 North Branch St.

Via Public Transit: The Green Mountain Community Network’s Brown Line stops at the White Rocks/Bald Mountain Trailhead parking lot. For more information, including current operating schedule, call 802-447-0477 and visit https://www.greenmtncn.org/nobenn-brown.html.

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In Lake Shaftsbury State Park:

Healing Springs Nature Trail – Accessible, Easy

This boardwalk sits at the southern end of Lake Shaftsbury and allows hikers of all abilities to cross a wetland and view the abundant wildlife it supports. For more information, visit https://vtstateparks.com/shaftsbury.html or call 802-375-9978.

Driving Directions to Lake Shaftsbury State Park:

Driving Directions to Lake Shaftsbury State Park:

From Bennington: Head north on VT-7A N. 1.5 mi after passing through the village of Shaftsbury, turn right on Lake Shaftsbury Rd at the state park sign. Park in the farthest most parking lot.

From Manchester: Head south on VT-7A S. 2.8 mi after passing Rte 313, turn left on Lake Shaftsbury Rd at the state park sign. Park in the farthest most parking lot.

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