The scenic Monadnock Branch Rail Trail travels for just over 7 miles from Webster Street in Jaffrey near the ball field to the New Hampshire–Massachusetts border. From Jaffrey to Rindge the trail is packed gravel, except for a paved section at the start in Jaffrey. The trail includes signage and beautiful views of ponds and wetlands. From Rindge toward Massachusetts, the trail is still undeveloped and is mostly packed gravel and sand, with some railroad ties still in place.

Locally, the trail is also known as the Jack Dupree Memorial Trail and the Rindge Rail Trail. The trail follows the old right-of-way of the Monadnock Railroad, an extension of the Fitchburg Railroad/Vermont and Massachusetts Railroad. The line served New Hampshire towns on the east side of Mount Monadnock, mainly Jaffrey and Peterborough.

To access the Jaffrey end, from the junction of NH-124 and US-202 in Jaffrey, head north on US-202. Turn right on Webster Street and park next to the trailhead by Legion Field.

To access the Rindge end, from the junction of NH-119 and US-202, head south on US-202. The parking lot (complete with map board) is on the left where the trail crosses US-202.

The TrailLink website has a description and map of a hike using the Monadnock Branch Rail-Trail.