Trail Running calendar near Canterbury 2025-2026

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.

Experience the 9th annual Wildcat 5K Trail Run, Walk and Wag on May 30, 2026 in Boxford, a scenic 5K around Stiles Pond through Wildcat State Forest. Runners, walkers and their dogs will enjoy trails, prizes and a festive post race celebrat..

Chocorua Mountain Race is a rugged 23K loop in the White Mountains that climbs Mount Chocorua and packs about 4,500 feet of ascent into technical trails and alpine views. Limited to 250 runners, it rewards strong trail skills and grit.

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.

Explore scenic trails south of Sebago Lake at the inaugural Otter Pond Trail Races in Standish, Maine on June 13, 2026. Choose a timed endurance Dawn to Dusk challenge, a 10K or a kids run while supporting Bonny Eagle Athletics.

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,..

Race The Cog invites runners to tackle the Mount Washington summit via the historic Cog Railway tracks on June 20, 2026, with 2.75 or 5.5 mile options. Expect steep, rocky terrain and a summit Cog train return for the shorter course.

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.

Test your limits at the Back Cove Backyard Ultra in Portland, ME, where runners complete a 4.16 mile loop every hour around Back Cove Park until one remains. Enjoy a flat scenic course, basic aid stations, and a friendly volunteer crew.

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.

Take on the Magnificent Bastards Challenge in Corinth VT, where runners and ruckers run repeated one mile loops with big climbs until one remains. Register by June 25 for guaranteed custom Race Mozey silkies; medals for long finishers.

Take on the rugged Baldface Scramble in Chatham NH July 25, 2026, with a challenging 29K or shorter 14K loop over the iconic Baldfaces with big climbs and alpine views. Technical, cupless trail racing for experienced mountain runners.

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..

Tackle rugged, high climbing trail ultras in the White Mountain National Forest with 20, 50 and 100 mile options. Expect technical trails, huge elevation, cupless aid and camping options for an epic mountain challenge.

Firebird Trail Races in Windham Falmouth Maine feature 50K, marathon and 13M races on technical single track through Lowell Preserve. Tackle rocky, root strewn trails with friendly aid stations and earn a carved wood Firebird medal.

Run the Triple Dam 10K in Perkinsville VT on August 23, 2026 for a scenic road and trail loop with a fun calf deep river crossing. Open to runners and walkers, proceeds support Springfield High School cross country.

Explore Waterville Valley trails at the Black Bear Trail Races on August 29. Choose from a family friendly 1 mile fun run up to a challenging 50K around nearby 4,000 foot peaks, with finishers awards, post race snacks and a finish festival.

Test your limits at the Last Man Standing Ultramarathon on September 5, 2026 at Pineland Farms in New Gloucester, Maine. Run repeating 4.2 mile wooded loops until a single finisher remains in this backyard ultra classic.

Trail Animals Running Club Fall Classic at Great Brook Farm State Park offers scenic trails and distances from 10K to 50 mile, plus a youth fun run and Mischief Mile. Aid stations and vegan options support runners in this cupless event.