The Monadnock Rail Trail Challenge, meant to encourage residents to explore the area’s Rail Trail, as well as the businesses around them, is being extended into 2026.
A partnership with the Greater Monadnock Collaborative, a regional Chamber of Commerce based in Keene, the challenge invites residents to explore regional rail trails, using any method — walking, biking, hiking, running, or on horseback — and use a digital passport to check in at participating businesses on or near the trails.
“Many towns are looking to put residents on their trails, for wellness reasons, for awareness of nature, for appreciation of the 115 miles that we have in the Monadnock Region to take advantage of,” said Vice President of the Monadnock Region Rail Trail Collaborative Bob Meissner. “In the Monadnock Region, [MRRTC President] Mike Kowalczyk designed a multi-year event that accomplishes many of the wellness-related issues in getting people out on the trail and adds a fun and economic related element.”
The challenge was launched last year, and is back again for 2026, with trail explorers able to participate through their self-paced exploration of the area around the rail trails, and collect points from “checking in” at participating businesses. The points can be redeemed for MRRTC swag, such as T-shirts, stickers and hats.
Five area rail trails are part of the challenge: The Cheshire Rail Trail, the Asheulot Rail Trail, the Fort Hill Rail Trail, the Monadnock Rail Trail and the Hillsborough Rail Trail.
There are participating businesses in Westmoreland, Keene, Swanzey, Hinsdale, Walpole, Troy, Fitzwilliam, Hillsborough, Peterborough, Jaffrey and Rindge.
Participating Peterborough businesses include the Monadnock Center for History and Culture and Aesop’s Tables. Jaffrey businesses include Jaffrey Pizza Barn, and Rindge businesses include Emma’s 321 Pub & Kitchen, Sandwich Master and Phoenix Smokehouse.
To create a passport to participate in the challenge, visit monadnocknh.com/visit-here/passports.