Please be aware that the northern half of Vermont was affected by major flooding. Roads to trailheads may not be open for the weekend, turn around if you encounter closed roads.

Chipman Hill

Chipman Hill has an elevation that is approximately 360 feet above that of the Middlebury town center and affords the hiker wonderful views. 
Trail Activity
Hiking Mountain biking Snowshoeing
5.10 miles, Network
Easy, Moderate
Middlebury (VT)
Packed Earth/Dirt, Gravel/Crushed Stone/Cinder
Permitted on leash


Chipman Hill, the most prominent geographic feature in the town of Middlebury, has an elevation that is approximately 360 feet above that of the town center and affords the hiker wonderful views. In the 1940s and 50s, Chipman Hill was the site of Middlebury College's downhill ski area, and even featured a ski jump, the remains of which can still be found. Since then, the forest has regenerated and the area is a favorite of walkers, hikers, and mountain bikers.

The Trail Around Middlebury (TAM) follows alongsome of the Chipman Hill trails.

Trail Manager

Visit Middlebury Area Land Trust or Middlebury Bike Club online for more information or contact:

Middlebury Area Land Trust

Middlebury Area Land Trust
PO Box 804
Middlebury, VT 05753
Phone: (802) 388-1007
View website
Addison County Bike Club
Middlebury, VT 05753
View website

Trail Tips

Plan Ahead and Prepare
Be prepared to find your way home. Familiarize yourself with the area before you set out and bring your map and compass along.
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Trailhead Information

Access is from Springside Street, High Street, or from the TAM trailhead off of Seminary Street Extension, just east of the Co-operative Insurance building.

Click on a parking icon to get custom directions
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