Trail Running calendar near Chester 2025-2026

Push your limits at Race for DFL, a backyard ultra at Kenty's Farm in Winchendon MA where runners repeat 4.1666 mile laps until only one remains. Choose 6, 12 or 24 hour options and enjoy themed laps, fun gear and great camaraderie.

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..

Test your grit at the Mount Ascutney Vertical Backyard, a Last Person Standing uphill race in Brownsville VT where runners repeat hourly laps of steep ascent until only one remains. Aid, indoor facilities and camping are available.

Join the 27th annual Novemberfest Race, a scenic 4 mile run through Mine Falls Park in Nashua on Sunday, November 23, 2025. Celebrate at Martha's Exchange with raffle prizes and beers while supporting the Nashua Children's Home.

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 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.

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 laps on a scenic 2 mile single track loop around White Lake in Tamworth, NH with 6, 12 or 24 hour timed options and a beach start and aid station. Costumes encouraged and bring your own hydration.

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 between 5 and 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..

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 8.2 miles and 3,010 ft of climbing at Killington Resort, summiting multiple peaks for sweeping mountain views. This limited field trail race tests runners on steep, rocky terrain with a memorable Needle's Eye finish.

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.

Take on Loon Mountain's Upper Walking Boss on July 12 in Lincoln, New Hampshire, a roughly one kilometer black diamond climb that will test every runner. Men, women and U20 categories plus a $1,500 challenge purse raise the stakes.