Trail Running calendar near Brownsville 2025-2026

Join Windham Woods School for the 2nd annual Thankful Trails 5K Run and Walk through scenic campus trails, plus a free Kids Fun Run on the Lower Field for ages 8 and under. Family friendly with raffle, awards, and lunch to celebrate communi..

Join the Novemberfest Race in Nashua for a scenic 4 mile loop through Mine Falls Park, followed by a lively post race party and raffle at Martha's Exchange. Community focused and fun, the event benefits the Nashua Children's Home.

Celebrate Thanksgiving in Springfield VT at Toonerville Trail Turkey Trot, a flat, scenic 5K along the Black River with a virtual option to support local food banks and school teams. Finishers get socks and cider donuts.

Join a scenic road and rail trail run with prizes for top finishers. Route may change for weather and the event will be canceled if it snows. Entry is donation based; proceeds benefit a local dog rescue and community theater.

Celebrate the Sunday after Thanksgiving at Gorge après Gorge in Chesterfield Gorge with a timed 5k, family fun walk, and new kids race. Finishers earn locally baked cookie medals and a warm postrace potluck to benefit Hilltown Land Trust.

Join Krampuslauf in Lyme NH for a festive mountain trail run from the Dartmouth Ski Way lodge, offering 5K, 10K and a 9 hour multi lap challenge. Finish loops to earn a 10K medal with pins and upgrades to a 50K medal.

Runamuck 50K is a rugged trail ultramarathon around South Pomfret, Vermont, weaving hilly dirt roads and scenic backcountry. Expect changeable weather and a true test of endurance on this challenging 50K course.

Run the scenic Dandelion Dash 5K on The Hartsbrook School trails or enjoy the family friendly Mushroom Mile in Hadley, MA. Support school programs in sustainable agriculture and beekeeping or run virtually from anywhere.

TARC Wapack and Back is a scenic, rugged trail race in May on the Wapack Trail between Massachusetts and New Hampshire, offering 21.5, 43 and 50 mile options. Expect technical terrain, big climbs, limited aid, and a tight knit trail communi..

Run the Free Spirit 50K in Leyden, Massachusetts and enjoy a scenic New England ultramarathon. The course follows dirt roads past historic farms, leafy woods and an 1870s covered bridge for a rewarding, challenging day.

The Canterbury Shaker Village XC 5k will take place in Canterbury on Saturday 16 May 2026. You can run 5 kilometers.

Infinitus is a multi day endurance festival May 21 to 30 in Ripton, Vermont, offering distances from 9 miles to the epic 888K 551 mile challenge. Set at Silver Towers near Green Mountain National Forest, it features dorm lodging, camping an..

Tackle the Chocorua Mountain Race, a rugged 23 km trail in the White Mountains with steep climbs, rocky singletrack and a summit loop over Mount Chocorua. Limited to 250 entrants, this demanding course packs 4,500 feet of elevation.

Run a scenic 5 mile route along the Cheshire Rail Trail from Fitzwilliam Depot to the restored Troy Depot while supporting the Fitzwilliam and Troy Historical Societies. Food, festivities and a short kids loop make it a great community day.

Take on the Cirque Series at Cannon Mountain on June 13, 2026: a rugged 6.9 mile mountain run with 3,080 feet of climb to a 4,031 foot summit in Franconia Notch. Expect steep, rocky terrain, epic views, and fierce competition across Sport,..

Take on scenic trails around Trapp Family Lodge in Stowe, Vermont on June 20, 2026 with 25K or 50K options. Enjoy rolling climbs through pastures and hardwood forest, stocked aid stations, and a festive finish at the Von Trapp estate.

Take on a rugged 8.2 mile trail in Killington Vermont with 3,010 ft of climbing. Summit Killington Peak and two others, tackle technical terrain, and vie for cash and gear in a field capped at 700 runners.

Scenic 5K and 10K trail races through the Green Mountain National Forest at Blueberry Hill Outdoor Center in Goshen. Proceeds support the center and registration opens Nov 1, 2025.

Tackle a scenic but rugged three day stage race around Lake Sunapee covering about 75 miles and 15,500 ft of climbing across technical single track, fire roads and gravel. Prefer one day? A 50k option follows the same corridor with roughly..

Jigger Johnson Ultras in Waterville Valley offers rugged White Mountain trail runs of 100, 50 and 20 miles with alpine summits and serious climbing. Courses are mostly unmarked so bring navigation skills and mountain safety gear.