Take on a short, steep hike with scenic Berkshire views
Approx. 1 hr
Up to 10 people
Local guide, trail snack
Explore Cheshire Cobble with a local guide on a small-group hike that leaves room for the rest of your day.
Meet your guide at the trailhead and get a quick overview before we start. We’ll hike up at a comfortable pace, take a few breaks as needed, and stop at the overlook to enjoy the Berkshire views and a light trail snack. Then we’ll make our way back down together.
Cancel at least 24 hours in advance for a full refund or credit. You'll also receive a full refund or credit if the operator cancels due to weather or other unforeseen circumstances. No-shows are charged the full price.
Product ID: M794E4
The guided hike accommodates up to 10 guests.
Bring a water bottle, light layers, and sunglasses or a hat. Wear weather-appropriate hiking clothes and comfortable hiking shoes or sneakers; closed-toe shoes are strongly recommended. Bring a small backpack if you'd like.
263 Windsor Rd, Cheshire, MA 01225
We had a fantastic ride along the Ashwillticook Rail Trail. The trail is flat and scenic and was a great fit for us as inexperienced riders. Our guide, Jenna, was informative, engaging and delightful. I highly recommend this experience.
Steve Clar
June 27, 2026
We had a fantastic ride along the Ashwillticook Rail Trail. The trail is flat and scenic and was a great fit for us as inexperienced riders. Our guide, Jenna, was informative, engaging and delightful. I highly recommend this experience.
Steve Clar
June 27, 2026
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