Trail Running calendar near Ashburnham 2025-2026

Explore trails around Soapstone Mountain and Shenipsit Forest at the Soapstone Mountain Trail Races in Stafford Springs, CT on May 17, 2026. Pick a half marathon or 6K, support local trail stewardship, and register January 1, 2026.

Take on the Drummer Hill Trail Races in Keene NH on May 23, with a 12.5k loop you can repeat for 12.5K, 25K, 37.5K or 50K. Expect technical single track, rocks, roots and stream crossings, aid stops and DHTR drumstick awards.

Hit the trails at the Wildcat 5K Trail Run Walk Wag in Boxford on May 30, 2026, for a scenic 5K through Wildcat State Forest with pond views and separate courses for runners and walkers. Enjoy post race treats, swag, and prizes for top fini..

Run a scenic 5 mile Cheshire Rail Trail from Fitzwilliam Depot to the restored Troy Depot on Saturday, June 6, 2026. Enjoy family fun, food, and festivities while supporting the Fitzwilliam and Troy historical societies.

Run a scenic 3 mile trail through farm fields and finish among the vineyard rows at Westport Rivers Vineyard and Winery. Celebrate after with wine, music, BBQ and a souvenir glass for a festive postrun party.

Explore rugged singletrack and an old railroad bed on a tough 5 mile loop at the Flat Rock Trail Race in Dunstable MA. Proceeds benefit the Humane Society for Greater Nashua and runners can repeat loops for up to six hours.

Run the scenic 15.7 mile Nipmuck South Trail at Mansfield Hollow State Park, following the Nipmuck Trail along the Fenton River through woods, fields and a climb to a cliff. Proceeds benefit Connecticut trail stewardship groups and the Blue..

Notchview Ultra invites runners July 10 to 13, 2026 in Windsor, MA, offering formats from 100.7 miles down to 6 hour on a scenic 1.9 mile loop. Enjoy frequent aid, camping, swag, and proceeds supporting local conservation.

Test your trail skills at the Spaulding Woods 50K, a challenging multi lap race on rocky singletrack and scenic footbridges around Northfield, New Hampshire. Well supported and community focused, the event benefits Spaulding Academy & Famil..

Soapstone Assault is a rugged 5.5 mile trail race with six steep climbs and about 1500 feet of climbing. Field limited to 50 runners and parking is tight, making this an intimate but fierce challenge with post race breakfast sandwiches.

Run the Ragged 75 multi day stage race or choose the single day 50k on rugged trails around Lake Sunapee, NH. Big climbs, scenic single track, communal camping and a true self supported trail challenge.

Join the Sweltering Summer Ultra, an 8 hour track challenge at Clapp Park in Pittsfield where runners and walkers lap a cinder loop and hit a marathon split. Chip timing, live leaderboard, refreshments and awards support the AYJ Fund.

Join an 8 hour trail gathering at Crandall's Park and run as many 5K loops as you like. Potluck, raffles, prizes and a Shenipsit Striders 50th anniversary gift for those who complete at least one loop.

Run the Triple Dam 10K in Perkinsville VT on a scenic loop of grassy trails, dirt roads and a shallow river crossing. Open to runners and walkers, this fundraiser for Springfield XC finishes by a swimming hole with post race treats.

Run the Old Goat Track Club XC Classic at Waters Farm in Sutton, a spike friendly 5K cross country loop and USATF New England Grand Prix stop. Perfect for teams and individual racers, with finish line snacks and a nearby after party.

Join the Trail Animals Fall Classic at Great Brook Farm for scenic trails and distances from youth fun runs to 50 mile ultras. Community vibe, limited spots, and on course aid make this a favorite, so bring your own hydration and register e..

The Mt. A Trail Challenge will take place in York Harbor on Saturday 19 September 2026. You can run 5 kilometers.

The Vermont 50 is a classic late September mountain bike and ultra run at Mount Ascutney offering 50 mile and 50K options, plus family fun and kids activities on Saturday. Proceeds support Vermont Adaptive Ski and Sports.

Run the newly restored Moosup Valley State Park Trail in Moosup CT with 5K, 10K and a kids fun run on Sunday September 27, 2026. Postrace medallions or tee shirts, food and drink, leashed dogs welcome, and proceeds benefit the Rotary Club o..

Run the winding single lane trails of Groton Town Forest with a choice of 9.5 mile or 3.4 mile courses featuring roots, rocks and rolling climbs. Limited to 250 runners, this community race supports Groton trail maintenance and finishes wit..