Trail Running calendar near Pittsfield 2026-2027

Experience a historic celebration of Scottish heritage at Loon Mountain Resort featuring heavy athletics, stone lifting, and traditional music amidst New Hampshire's scenic fall foliage.

Experience the scenic Trail Around Middlebury with distances ranging from a 2 mile fun run to a full 19 mile loop. This trail event features beautiful mountain views and technical single track sections in Wright Park.

The Route The Westmore Mountain Challenge is a one-day event covering five mountains and approximately 26 miles. The route includes Moose, Hor, Pisgah, Haystack, and Bald mountains. The course uses public trails and roads, with a cumulative..

Experience an endurance tradition at Mt. Ascutney featuring 50 mile and 50 km ultra runs, mountain bike races, and team relays. This scenic event supports Vermont Adaptive and includes fun races for kids.

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..

Run for conservation at the 10th annual Amy's Adventure Race. Choose from 4.5-mile or 10-mile trail courses through Amy's Park in the Adirondacks. Your entry supports the Lake George Land Conservancy and includes a post-race celebration.

The Buck 50 is a 50 km ultra that tackles four of Lake George's tallest peaks in the southern Adirondacks. With 9000 ft of climbing on rugged trails, it's a demanding point-to-point loop starting and finishing at Camp Chingachgook. The even..

Enjoy autumn trails at the Keene Family YMCA Fall Foliage Trail Races on October 4, 2026, with 5K and 10K options around scenic Keene, NH. Run for community impact while enjoying chip timed courses and seasonal views.

The Mile for Mentoring will take place in Gilford on Sunday 4 October 2026.

The Devil's Den Ultra challenges runners on a rugged 6.4-mile Vermont trail loop. Choose from a 30-hour, 12-hour, or single-loop 10K race. Every finisher earns a unique Devil tarot card, with more cards awarded for major milestones in the t..

A fall trail marathon and half marathon on the scenic Trapp Lodge trail system in Stowe, Vermont. The course features a mix of wide paths and rugged single track with significant climbs and descents. Participants will run through the colorf..

Explore the scenic trails of 100 Acre Woods in Malta, New York. This community event on October 18, 2026 features 2k, 3k, and 5k trail runs. All proceeds support local trail maintenance.

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.

The UltraTrax Burke Mountain will take place in Burke on Sunday 25 October 2026. You can run between 7 and 28 miles.

Tackle a unique mountain course that goes up and down four times over 4.9 miles. The event offers prize money, age group awards, and benefits the Keene Community Kitchen. Early registration includes a t-shirt.

The Moreau Half on October 31, 2026, tackles 14 miles of technical singletrack in Moreau Lake State Park, featuring 2,700 feet of elevation gain. With a start and finish at the park beach, this challenging trail run includes one aid station..

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..