Monadnock Rail Trail NH

• 4-star trail
• 8.9 miles each way
• Medium difficulty | Easy - Moderate elevation
• Jaffrey - Winchendon, MA | Monadnock Region
• Driving Directions: Marked on map

Railroad tie bridge over Robbins Pond.

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The Monadnock Recreational Rail Trail is located between the towns of Jaffrey, NH and Winchendon, MA on the Southern border of New Hampshire. It also incorporates the Rindge Rail Trail and the Jack Dupree Memorial Trail.

Although the official length of the Monadnock Rail Trail is 7.5 miles, we have mapped the full 8.9 mile trail into Massachusetts, including identifying abandoned routes and alternative trails to continue your journey. The link to the map is at the bottom of this article.

The Monadnock Railroad route was carved into the landscape in 1870 and extended North to Peterborough a year later. The line remained operational until 1984. To explore this route to its fullest, we recommend beginning in the town of Jaffrey and heading south. Paved trail gives way to dirt and compacted crushed stone when you leave the town behind, as you follow first the Contoocook River then cross the Contoocook Lake with water on both sides of you. Pass through wetlands, then briefly follow the US-202 until you head off into dense woodland.

Asphalt, Hardpack, Rough, No Access, Parking Expand Map

Monadnock Rail Trail 4★
8.9mi ea way, Medium, Elevation nominal.
Trailspotting Map: AllTrails, GPX File

Trail conditions are good for bikes with at least hybrid tires, which is what we used for the journey. There is a short section with railroad ties, a couple of brief spots of sand and one short patch of track ballast – all easily overcome.

Mile 7.5 is where you’ll find the state boundary marker, and this is where most published maps of the Monadnock Rail Trail route end. However, you should at least check out the railroad tie bridge at Robbins Pond just a little further South, and we also recommend continuing South as long as conditions allow. We tackled this trail in a wet, late August and found the remaining trail to Winchendon to be fine for the most part, with occasional patches of shallow mud.

If you’re able to reach the outskirts of Winchendon you’ll be presented with a pile of junk blocking your path. In case you want to go further, we’ve mapped a couple of routes to reach public roads that will lead you to the final part of the old railroad route into Winchendon – which is around 1,100 ft long and unimproved.

Trail Conditions: Asphalt in Jaffrey for 0.4 miles then 7.1 miles of hardpack trail to the state line. Further South trail gets rougher and possibly waterlogged.

A rusted railroad spike atop the state boundary marker.

Industrial dilapidation in Winchendon, MA.

• External Links: Public Map at AllTrails
• Facebook Group: Comment on this article

Nearby Trails:
• Show on map: All nearby trails

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