Trail Running calendar near Milton 2026-2027

Test your limits at the birthplace of Spartan Race in the Green Mountains of Vermont. Choose from distances ranging from 5km to 50km featuring steep climbs and rugged off trail descents at the iconic Killington Ski Resort.

Experience the scenic Trail Around Middlebury with distances ranging from a 2 mile fun run to a full 19 mile loop. Enjoy single track trails and mountain views in this community event supporting Vermont footpaths.

Trail du Parc National de la Yamaska offers five trail distances on rolling, low technical forest paths along the Choinière reservoir, plus a children's race and on site bib pickup.

A community-focused mountain running event in East Charleston, Vermont on September 26, 2026, crossing five peaks on mainly single-track trails. Timed full marathon and 20 mile trail only options are offered while proceeds support NorthWood..

Experience the inaugural Cirque Series at Jay Peak featuring a 7.1 mile course with over 3000 feet of vertical gain. Runners navigate technical terrain and rocky ridges to reach the summit for 360 degree views of the Vermont landscape.

Trail and obstacle race based on police training presented with the Royal Canadian Mounted Police. Two 2026 dates in Québec and Montréal, multiple distances and solo or team formats, plus an elite wave and fundraising for pediatric research..

Hit the Trail 2026 offers a timed 5K run/walk or bicycle rides on Vermont's scenic Lamoille Valley Rail Trail. The event raises funds for healthy aging services in Central Vermont. Join the community in Morrisville on September 27 for a day..

Experience a rugged trail race through the Adirondack forests and wetlands of Amy’s Park. Enjoy scenic views and a community after party at a local brewery while supporting land conservation for Lake George.

Devil's Den Ultra in Bradford, Vermont on Oct 10 to 11 2026 uses a 10K loop on Wrights Mountain and offers 30 hour, 12 hour and 10K options. Entries are capped at 100 and finishers receive tarot style awards.

Le Cross des Couleurs offers multiple race distances on Sunday October 11 at the Base de Plein Air. Courses are secured with free race photos and medals for all finishers and for the top three in each age group.

Trail running and mountain biking in Bromont with distances from 2 to 160 km, focused on fundraising for many causes. The 13th edition takes place in October 2026 and channels donations through L'Effet BU.

Trail races at Trapp Family Lodge in Stowe, VT on Oct 17, 2026 include a half marathon and a full marathon that is two laps of a 13.1 mile loop with singletrack, dirt roads and steep climbs to Round Top Mountain.

Trail running at Cap-Saint-Jacques offering distances from 1 km to 21.1 km with official timing, limited water refill points and group discounts. Practical details include parking options and eco-responsible rules.

This Halloween-themed 5K trail run takes place on the Laura’s Tears trail at Arrowhead Golf Course. Awards are given to the top finishers, and costumes are encouraged. Refreshments and facilities are available.

Experience a timed mountain trek across the rugged ridges of Vermonts Northeast Kingdom. Choose from multiple loop distances and the option to carry weighted gear for an added challenge on the scenic trails of Burke Mountain.

Race Mozey brings the Central European Krampus Run tradition to New England. Choose from a 5K, 10K, or a 9-hour challenge to complete laps at the Dartmouth Skiway. Finishers get medals, and the event supports Vermont Adaptive Ski and Sports..

Experience a unique indoor run through Montreal's famous RESO underground city. This 5 km challenge takes you from Cours Mont-Royal to Complexe Desjardins away from the winter cold.