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Hillwinds Trails

3.7 miles of woodland trails used by hikers, trail runners, and mountain bikers.
Trail Activity
3.7 miles, Network
Easy, Moderate
Brattleboro (VT)
Packed Earth/Dirt


The Hillwinds Trails system consists of 3.7 miles of trails near the northern border of the Town of Brattleboro. The trails are popular with hikers, trail runners, and mountain bikers.  

The main 2.7-mile trail network is in a mature white pine forest. A loop here using the Upper Trail and Beaver Pond Trail is 1.8 miles; other loop options are possible with the Connector and Ridge Trails. Mountain bikers will find the moderate width singletrack trails to be of beginner or low intermediate technical difficulty.

A 1.0-mile side trail recently opened to the public extends uphill to Pleasant Valley Road (there is no parking or signage on Pleasant Valley Road). This trail is steeper and rougher than the main trails, and of intermediate difficulty for mountain biking.

A trail map can be found on the Town of Brattleboro website below, in the Sports and Recreation Section.

Other Information

The Hillwinds Trails are managed and maintained by the Hillwinds Conservation Lands, Inc., a nonprofit organization comprised of two-dozen homeowners and adjacent landowners. These trails have been made available to the public through the generosity of this organization and a neighboring private landowner, in cooperation with the Town of Brattleboro Conservation Commission.

Trail Manager

Please visit the Town of Brattleboro online for a printable map and more information, or contact:

Brattleboro Conservation Commission

Brattleboro Conservation Commission
c/o Planning Services Department
230 Main St, Suite 202
Brattleboro, VT 05301
View website

Trail Tips

Plan Ahead and Prepare
Know how to choose and use your gear for each trip, factoring in the terrain and conditions.
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Trailhead Information

Follow VT-30 north out of Brattleboro and turn left onto Upper Dummerston Road (just beyond the Retreat Farm & Grafton Cheese). Follow Upper Dummerston Road 2.3 miles and turn left onto Hillwinds Road. In 0.2 miles, turn right onto Hillwinds North and drive to the end. The trails begin on the left.

Note: the "No Parking" signs are there to discourage parking during snow removal. The Town assures that there is no general parking prohibition here.

Click on a parking icon to get custom directions
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