The town of Bolton has an extensive network of trails. The best information on them is located on the Bolton Trails website.
This page focuses on Rattlesnake, a 453 acre parcel laced with trails and many natural features such as rock outcroppings, caves, and vernal pools and some historical features like quarries and mills. The trails consist of old cartpaths and singletracks. There is a mix of beginner and intermediate terrain with some advanced sections with typical New England rocky sections. The trail junction markers are useful for navigating the trail network, but only with a reference map on hand. There are multiple areas to park, but most people park in the lot directly visible from State Route 117 (195 Main Street, Bolton, MA) . Be sure to check out the Ridge Loop Trail and Boulder Trail. Longer rides can be connected to adjacent properties within Bolton, Harvard, or Stow.
Some of the trails at Rattlesnak will bite you if you're not careful. Nest not to ride here the morning after a rainstorm.
Note: All trails in Bolton are dog, equestrian, and mountain bike friendly.
Get a better idea of the avilable trails in Bolton by looking at the Town Trail Map.
ProTip: End your ride with BBQ, pizza, and beer at Slater's (outdoor seating + view of parking lot