Cheshire Cobbles Trail

MODERATE 22 reviews

Cheshire Cobbles Trail is a 2.1 mile moderately trafficked out and back trail located near Cheshire, Massachusetts that features beautiful wild flowers. The trail is rated as moderate and primarily used for hiking, walking, nature trips, and birding. Dogs are also able to use this trail but must be kept on leash.

2.1 miles
830 feet
Out & Back

dogs on leash

kid friendly



nature trips



wild flowers



10 days ago

Beautiful view!!! Follow the white markers. Best to use GPS from alltrail app due to some of the trail is poorly marked.

28 days ago

Views were awesome!

7 months ago

Great short hike! Not as steep as I would have expected. Took about 1.5 hrs round trip with 15 minutes at the top, and parking at the rail trail parking in Cheshire. No parking at trailhead. Return to Cheshire by AT North- white blazes, trail has a few turns so keep an eye for blazes. Views were awesome at the top!

8 months ago

Short, steep trail leading to fantastic views to the north, west and south.

8 months ago

9 months ago

9 months ago

Parking area is on Notch Rd.

10 months ago

Google maps via this app brings you to the end of Furnace Hill Road, a residential area with no parking sides on both sides of the street. Can someone please post where the parking is for this hike?

Sunday, May 15, 2016

when you get to the red arrows pointing back the way you came, follow them backward and around to the left away from the AT for about 100 ft.

Thursday, April 28, 2016

Gorgeous view and perfect workout

Friday, April 22, 2016

The scenery was beautiful. The hike was very pleasant. Will do it again for sure. Had a awesome picnic on the top of the cobble looking out at Cheshire Lake.

Wednesday, March 30, 2016

Great views. Got lost on the way up. Follow single white markers not the double when you come to the fork.

Monday, November 02, 2015

Beautiful hike with amazing views

Sunday, October 18, 2015

Cold, short hike. Steep incline but overall easy hike. The view is spectacular.

Monday, August 31, 2015

Friday, April 03, 2015

Accessed via the AT. Absolutely beautiful views. Greylock is visible in the distance on a clear day.

Saturday, December 27, 2014

Thursday, November 06, 2014

just hiked this trail for the first time. The view was so awesome. Plan to again soo.

Friday, May 09, 2014

First time on the trail and I loved it! I am going to do this trail more often. The hike up the hill was rough for someone out of shape but it was worth it for the view! The view was better than I thought. I could of stayed up there for hours.

Monday, December 09, 2013

Good parking and access. You'll follow a footpath until hits the Appalachian Trail that is marked by signs and yellow paint/markings, I believe you're suppose to follow the AT up to the overlook. I got side tracked by the multiple trails, footpaths and logging trails, so be careful.