Trail Running calendar near Randolph 2026-2027

Join the Millstone Madness Snowshoe Race on Feb 7 in Websterville VT for a scenic 3 mile loop around old granite quarries on single and double track trails. Snowshoes are required; enjoy friendly competition, prizes, warming fire and raffle..

Join Bradbury Mountain Winter Roulette on Sunday February 15 2026 for an unpredictable winter trail challenge of about 5 miles. Course and gear change with weather so expect deep snow, icy pack or bare trails and check for final details.

Take on winter trails at Défi des Collines Enneigé in Sainte-Catherine-de-Hatley on Saturday 21 February, with distances from 5.5 km to 30 km perfect for spring marathon prep. Finish to a medal, post race meal and a friendly community atmos..

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.

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

Join a lively multi day trail running festival at Pineland Farms on May 23 and 24, 2026, with races from 5k to 100k plus live music, food and a beer garden. Spectators welcome and camping is available for weekend racers.

Run a rugged 23 km course in the White Mountains with a summit loop over Mount Chocorua. Steep climbs, technical singletrack and stream crossings deliver 4,500 feet of climbing and unforgettable alpine views.

Race the Cirque Series at Cannon Mountain on June 13, 2026, a rugged 6.9 mile climb to the 4,031 foot summit with 3,080 feet of gain. Expect rocky, steep trails and sweeping views on this demanding mountain course.

Explore the inaugural Otter Pond Trail Races in Standish ME, with a scenic 10K, Dawn to Dusk challenge and a kids' fun run around Sebago Lake. Tackle technical single track and marked loops while supporting Bonny Eagle Athletics.

Race The Cog sends runners along the Cog Railway from Bretton Woods to Mount Washington's summit, offering 2.75 mile and 5.5 mile options. Expect steep climbing, dramatic views, and alpine weather for a true mountain challenge.

Run scenic loops around Trapp Family Lodge on June 20 in Stowe Vermont with 25K and 50K options. Wide hard packed trails wind through pastures and hardwood forest with well stocked aid stations for a scenic, challenging race.

The Ultratrax Cranmore will take place in North Conway on Saturday 27 June 2026. You can run between 7 and 28 miles.

Join East Bayside Trail Fest in Portland for a timed Trail to Ale 10K, 15 and 30 mile group rides, or a family friendly 2 mile. Finish on Diamond Street with music, food trucks and local brews while benefiting local trail and bike groups.

Celebrate July Fourth with the Freedom Run in Newport and Derby, a run or walk along gravel paths and wooded trails. Pick a distance up to a half marathon, enjoy post run ice cream and watermelon, and support NAMI Vermont.

Take on a technical 50K in Spaulding Woods New Hampshire, six rugged laps of rocky singletrack, roots, footbridges and about 4,400 feet of climbing. Aid stations and drop bags support runners chasing a 10 hour cutoff.

Take on the Summer Hill league at Ardwhallan Outdoor Pursuit Centre in West Baldwin on Sat 18 Jul 2026, a testing 4.5 km trail with 150 m of climb. Pre entry is required and junior entries welcome for a fun, competitive summer race.

Baldface Scramble in the White Mountain National Forest offers 29K and 14K routes over steep ledges and exposed ridge lines, with sections that require scrambling. Expect big climbs, mandatory safety gear and a mountain trail challenge.

Celebrate the 10th anniversary Ragged 75 around Lake Sunapee, a three stage trail challenge of about 75 miles with 15,500 ft of climbing, or tackle the one day 50k of roughly 33 miles. Camp by the lake, race rugged trails and push your limi..

Jigger Johnson Ultras offers rugged, technical trail races in New Hampshire's White Mountain National Forest, August 14 to 16, 2026. Choose 20, 50 or 100 mile routes that test navigation, endurance and reward big mountain views.

Firebird Trail Races on August 22, 2026 send runners on scenic single track loops through Lowell Preserve and North Falmouth Community Forest, with 13M, marathon and 50K options. Enjoy volunteer supported aid stations and a wood carved Fire..