Pine Cobble Preserve Williamstown Rural Lands Foundation Chestnut Trailhead
Chestnut Hill, Williamstown, MA

Activites & Features
  • Dogs allowed
  • Free
  • Scenic View
  • Trailhead
Safety Tips
Chestnut Trailhead in Williamstown, MA | Berkshires Outside
  • Public Land
  • Private Land
  • Bus Route
  • Trail
  • Major Trail

About Chestnut Trailhead

The Chestnut Trailhead leads to an extensive hiking area in Williamstown. Upon arrival, visitors will see a narrow hiking trail traveling into the forest. The path will climb steadily up the mountain, passing alongside tall trees and interesting rock features. Then, hikers will reach a fork.

Going right, visitors will hike on a connector trail and meet the Pine Cobble Trail. Plenty of Western Massachusetts wildlife is visible from the path, including wildflowers and salamanders. The trail eventually rises to "Pine Cobble:" a rocky outcropping with panoramic views of North Adams and Williamstown.

Toward the left at the trail junction, meanwhile, visitors can continue on the Class of '98 trail until it meets the Appalachian Trail. This long-distance pathway, which travels from Georgia to Maine, heads northward to the Green Mountains of Vermont. Hikers there will find the start of the Long Trail (another long-distance pathway), about seven miles from the trailhead. Overall, the Chestnut Trailhead is an excellent launch point for travelers beginning their thru-hike.

The Pine Cobble Trail also connects with the Appalachian Trail, meaning that hikers can follow the AT and loop back to the parking lot on either trail.

Visitors will find parking on the shoulder of Chestnut Street. The parking area offers scenic views of the Berkshires toward the west.

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Chestnut Hill, Williamstown, MA

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Clubs, Retail & Rentals

Looking to meet up with others for team sports or group activities? Check out our list of clubs and leagues in the Berkshires. We also link to an array of outdoor recreation resources: retail shops for gear, rental facilities for equipment, and guides to get you where you want to go! Our list of summer camps will help you plan an overnight or day camp adventure for your young ones.