Trail Running calendar near Milton 2025-2026

Join the festive Krampuslauf at Dartmouth Skiway in Lyme NH with 5K and 10K trail courses or a challenging 9 hour timed event of repeated 10K laps. Earn a 10K medal after your first lap and collect pins and upgrades as you go.

Celebrate New Year’s Eve with a scenic, untimed run or walk along the Burlington bike path with 1 mile, 5K, or 5 mile out and back options. Gather by the ECHO Leahy Center, then enjoy live music, the burning of Champ and fireworks.

Tackle snowy hills in Sainte Catherine de Hatley with 5.5, 11, 15 and 30 km road or trail routes and online maps. Warm up at aid stations, earn a medal and enjoy a hearty post race meal in a festive winter atmosphere.

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.

Infinitus is a multi day endurance event in Ripton, Vermont from May 21 to 30, 2026, with races from 9 miles to 551 miles for novice to elite ultra runners. Held at Silver Towers near Green Mountain National Forest, camping and dorm lodging..

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.

Tackle the scenic Catamount Ultra at Trapp Family Lodge in Stowe, VT with a 25k route or a two lap 50k that winds through highland pastures and hardwood forest by Mount Mansfield. Expect big climbs, sweeping views, helpful aid stations, and..

Conquer Killington's peaks at the Cirque Series on June 27, 2026, an 8.2 mile mountain run with 3,010 feet of climbing and sweeping Green Mountain views. Expect steep technical terrain, two aid stations and a field capped at 700 entries.

Celebrate July 4 at Whiteface Mountain with summit finishes, sweeping alpine views, and a gondola ride back to the base. Choose a 10k, 21k, steep Ascent, or Kids Ascent for a challenging mountain run and unforgettable scenery.

The Harry Corrow Freedom Run will take place in Newport on Saturday 4 July 2026. You can run between 5 and 13 miles.

Run through the Moosalamoo National Recreation Area at the Goshen Gallop, a friendly trail event offering 10K and 5K routes across ski trails and gravel roads. Support local trail stewardship while enjoying a scenic Vermont race.

XTERRA Bromont on August 22 23 2026 brings off road triathlon, gravel duathlon and trail runs at Lake Bromont and the Olympic Equestrian Park. Distances for all levels plus World Championship slots.

Run the rugged Kilkenny Ridge across iconic White Mountain peaks with 25K, 25 Miler or epic 50 Miler options featuring big climbs and remote singletrack. Expect self navigation, mandatory safety gear and a true alpine trail adventure.

Run five Northeast Kingdom peaks in the Westmore Mountain Challenge, a mountain marathon through peak fall foliage on scenic trails. All proceeds benefit NorthWoods Stewardship Center and local trail conservation.

Run Amy's Adventure Race for the Lake in Bolton Landing, NY through scenic Adirondack trails. Choose 4.5 or 10 mile courses or run virtually, enjoy lake views and a postrace beer while supporting the Lake George Land Conservancy.

Take on the von Trapp Mountain Marathon at Trapp Family Lodge in Stowe Vermont with half and full options on a rugged 13.1 mile loop featuring steep climbs and a summit scramble to Round Top. Enjoy sweeping views of Mount Mansfield and a th..

Join the Ghostly Gallop Trail 5K on Sunday October 25 in Milton Vermont for a spooky run along the Laura's Tears trail at Arrowhead Golf Course. Costume friendly with prizes, post race refreshments, and family fun.