Hillsborough Recreational Rail Trail Activities and Amenities This trail begins at Union Street in Hillsboro and runs 8 miles to where it ends near Bible Hill Road by the Monadnock Paper Plant. The trail crosses old RR trestles and passes by historic mill sites as it follows the Contoocook River. Hillsborough Recreational Rail Trail Map Parking Areas Deering: 57 Fish and Game road, Deering (private shooting club not the state agency) has a parking lot right next to Long Woods Rd. Google maps has “Hillsboro rec trail” for parking lot. (43.090347, -71.906876). Organizations that work in with the Bureau of Trails to help maintain this trail are: Night Riders, Inc.