Trail Running calendar near Winchendon 2025-2026

Mount Ascutney Vertical Backyard, in Brownsville, Vermont, is a Last Person Standing endurance race on Mount Ascutney. Runners ascend and descend the mountain hourly, with two ascent options: a three-lap orange loop up the t-bar path for 403 vertical feet per lap, or a single ascent on the green loo..

The 27th Annual Novemberfest Race for the Nashua Children’s Home is a festive 4-mile run through Mine Falls Park in Nashua, New Hampshire. Runners traverse scenic park trails, finishing near the Pine Street Extension Entrance. The post-race celebration and raffle take place at Martha's Exchange Rest..

TARC Winter Classic is a trail ultrarunning event at the Middlesex Fells Reservation in Stoneham, MA. Runners choose 8, 32, or 40 miles, starting and finishing at Fallon Road. The Skyline Trail offers a rugged New England course of roots, rocks, and elevation, with constant climbs and descents and o..

Krampuslauf in Lyme, New Hampshire, at the Dartmouth Ski Way, offers 5K, 10K, and a 9‑hour endurance option. Runners begin at the base lodge and tackle Holt’s side for a steep 5K ascent; 10K participants complete Holt’s and then Winslow side before finishing by the lodge. The 9‑hour loop repeats the..

The Mount Hood Nutcracker Challenge is an annual cross-country running event held at the Mount Hood Golf Club in Melrose, Massachusetts. This unique 3.5-mile race features a challenging, hilly course that changes every year, incorporating fairways, paved cart paths, road crossings, and wooded sectio..

The TARCtic Frozen Yeti, hosted by the Trail Animals Running Club at Hale Reservation in Westwood, Massachusetts, offers a 15-mile option split into three roughly five-mile loops starting and finishing at Powissett Lodge. The Red, Blue, and White loops are clearly marked with pink ribbon and reflect..

Located in Union, Connecticut, the Northern Nipmuck Trail Race is a 16-mile ultramarathon staged just outside Bigelow Hollow State Park. The course runs south on the Nipmuck Trail through the Yale-Myers Forest, crosses Barlow Mill Rd at mile 4, then reaches a turnaround at Boston Hollow before retra..

Run Across CT is a coast-to-coast ultramarathon across Connecticut, starting in East Thompson and finishing at the Wakeman Boys & Girls Club in Southport. The course covers 123 miles and is offered as Solo 100k or Solo/Relay 200k (3–6 person teams). Runners traverse 25 towns, with about 57 miles on..

The Merrimack River Trail Race will take place in Andover on Saturday 11 April 2026. You can run between 10 and 10 miles.

Join Trail Animals Running Club for the TARC Spring Classic at Jericho Town Forest in Weston, Massachusetts. The event offers 10K, Half Marathon, Marathon, and 50K distances, with a flat, smooth course crafted around a single 10K loop repeated for longer distances. Start/Finish at 292 Concord Road.C..

Trail Animals Running Club's Wapack and Back takes place in Ashburnham, Massachusetts, along the Wapack Trail from Mount Watatic to North Pack Mountain in Greenfield, NH. Runners choose among 21.5-, 43-, and 50-mile ultramarathons. The course features rocky ledges, boulder fields, granite slabs, and..

The Wildcat 5K Trail Run-Walk-Wag is an annual event held in Boxford, Massachusetts, starting and finishing at the Danvers YMCA Camp overlooking scenic Stiles Pond. The race features separate courses for runners and walkers, including those with dogs ("waggers"), winding through the Wildcat State Fo..

The Nipmuck South Trail Race is a 15.7-mile out-and-back trail run held in Mansfield, Connecticut, starting at Mansfield Hollow State Park. The course follows the scenic Nipmuck Trail alongside the Fenton River, featuring varied terrain including small bridge crossings, a climb to a 50-foot cliff, f..