Cheshire Rail Trail The Cheshire Rail Trail is a 42-mile rail trail with a mostly gravel and dirt surface that runs through Westmoreland, Keene, and Troy, with endpoints in Fitzwilliam and Northern Walpole. The full trail is considered a moderate hike covering 37.4 miles with 2,027 feet of elevation gain and takes approximately 12.5–14 hours to complete. This multi-use rail-trail accommodates mountain biking and horseback riding, and in winter, cross-country skiing and snowshoeing. Key highlights include the Stone Arch Bridge near the Keene trailhead, historic railroad remnants, and numerous water features along the way. Notable features include direct access to Stonewall Farm, passage over the historic Arch Street stone arch tunnel, and glimpses of deeply carved railroad beds visible in multiple locations.