Explore the best rated trails in Winchester, MA, whether you're looking for an easy walking trail or a bike trail like the Southern New England Trunkline Trail and Heritage Trail (NH) . With more than 108 trails covering 673 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
The trail in Cranston was repaved recently. There weren’t even lines painted yet! It was a smooth ride. There was one detour due to the paving, but it was an easy ride on a side street.
I'm in love with this trail. Much of the trail path is dirt, but there is a new area with fine gravel. I find this such a peaceful trail and consider it to be in good maintenance. Thanks to everyone that maintains the trails.
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