Cheshire Recreational Rail Trail Activities and Amenities This 42 miles of trail runs from Fitzwilliam, Troy, Keene, Westmoreland, North Walpole.This trail includes a beautiful arch bridge over the Ashuelot River.There is a break in the trail through the Town of Keene. It can be picked up again at Island Street. NH State Parks blog: From Rail Road to Rail Trail Parking areas Troy: Limited parking in Troy on Water St next to the RR Depot (42.724676, -72.184249) Fitzwilliam: Big lot in Fitzwilliam off of Old Turnpike Rd (42.723591, -72.093055) at Sip Pond Trailhead. This lot was built by the Monadnock Conservancy. Nice kiosk. You can also park nearby at the trailhead on State Line Cir in Fitzwilliam (42.718686, -72.083602). Google maps has this location as “Cheshire Rail Trail”. Organizations that work with the Bureau of Trails to help maintain this trail are: Pathways for Keene Monadnock Sno-Moles Westmoreland Sno-Belters Hooper Hill Hoppers