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If you’re searching for scenic, dog-friendly trails in the Berkshires, the Ashuwillticook Rail Trail in Cheshire, MA, is a standout destination. This well-maintained paved trail features accessibility for both wheelchairs and strollers, making it easy for everyone to enjoy the surrounding nature. Dog owners will appreciate that dogs are allowed throughout the trail, perfect for those seeking a beautiful spot for a leisurely walk, invigorating hike, or a day out with family and pets.
The Ashuwillticook Rail Trail is known for its stunning scenery—especially during the fall foliage, family-friendly amenities, and wide paths ideal for biking, running, or walking your dog on-leash. With plenty of parking, public restrooms, picnic tables, benches along the route, and good maintenance year-round, visitors and their pets can enjoy a hassle-free outing. Come and discover why this pet-friendly trail in Cheshire, MA, is a local favorite for both adventure and relaxation!
What a nice trail. My wife and I biked the trail. We starting at the trail parking lot near the old mall and did 20 miles total. 10-miles out & back. The trail is asphalt and very well maintained. A lot of consideration when into the road crossing. I notice a small shop that serves ice cream. What missing is a indoor/outdoor cafe along trail that serve coffee, smootie, pastry. Job well done by those who plan, designed and maintained this trail.
10.7.22 I absolutely love this trail and I use it foe bike riding. Lots of parking, porta potties, benches to stop along the way, paved, and you can’t get lost. And best of all, family friendly with spectacular views, especially in the fall.
Great trail, any season. Well maintained and great for running, or biking. Plenty of room/space even on crowded days
We stumbled upon this trail during one of our spontaneous trips to the Berkshires, and it turned out to be a hidden gem. The scenery was absolutely breathtaking, with vibrant fall colors painting the landscape. The trail offered a perfect blend of adventure and romance, making it ideal for either a leisurely stroll or an invigorating hike.
As we walked hand in hand, the crisp autumn air and rustling leaves created an enchanting atmosphere. The trail winds through stunning views, with the birch trees standing tall and majestic, adding to the overall charm. Whether you’re looking for a peaceful escape or a bit of adventure, this spot is perfect for embracing the beauty of nature on a fall day. We left feeling rejuvenated and inspired, already planning our next visit!
It is springtime in the Berkshires, the birds are singing and the trees are dressing up. It wonderful place to be. The trail is maintained well.