Trail Running calendar near Gilford 2026-2027

Keene Family YMCA Fall Foliage Trail Races feature 5K and 10K trail courses starting and finishing at the Keene YMCA, with chip timing, age-group prizes, and proceeds supporting YMCA programs and access.

A one-mile community event in Gilford, New Hampshire on October 4, 2026, with categories for adults, youth, and children and a complimentary shirt for those who register before September 16.

Trail running at Tibbetts Field in Madbury includes a 5K and a 1 mile fun run over natural terrain through Powder Major Forest, with proceeds supporting youth recreation scholarships.

Experience the peak of New England autumn on a journey through the mountains and fields of central Massachusetts. This trail event offers three distances crossing state borders for runners seeking adventure on the Midstate Trail.

A multi-distance trail event on Wright's Mountain in Bradford, Vermont, featuring 30-hour, 12-hour and a shorter loop race. Finishers receive themed tarot cards and awards, with the field capped at 100 runners.

The 26th North American Wife Carrying Championship returns to Sunday River in Newry, Maine on October 10, 2026. Teams of one man and one woman race a 278 yards obstacle course with log hurdles, a sand trap, and the Widow Maker water hazard.

A rugged trail race at Pawtuckaway State Park featuring technical terrain, boulders, streams and a rocky climb. It offers a half marathon and a 5 mile option and lists $7500 in prize money for 2026.

A human powered 100k in Norway, ME combining 25k running and 75k cycling across six trail systems. Solo and duo formats, cupless aid stations, and proceeds supporting local youth and land trust programs.

A multi format trail event on the Granite Town Rail Trail in Brookline and Milford NH on October 17 and 18 2026, featuring 7.5 mile relays, 15 mile and 30 mile races and a 30 hour ultramarathon. Proceeds support local trail conservation.

A mountain running event in North Conway, NH on October 17, 2026, featuring two race options on Cranmore Mountain and $7500 in cash prizes. The course uses ski slopes, singletrack, and service roads and includes one aid station.

A trail event at East Windham Conservation Area offering a five loop 50k and a single loop 10k with two aid stations per loop and volunteer support. Finishers receive a cotton event t shirt.

A 4.1 miles trail race in Ravenswood Park, Gloucester, held October 18, 2026, as part of the North Shore Trail Series. The course uses single-track and carriage roads, with online registration closing October 15 and race-day registration av..

A 5K on October 24, 2026 at Stratham Hill Park that runs along Great Bay and benefits Great Bay Stewards; the mostly downhill course includes a race shirt for timely registrants and a bib with a beer or cider coupon.

A 4.9 mile mountain trail race in Keene, NH on October 25, featuring four up and down laps on different trails, 1650 feet of elevation, prize money and age group awards, with proceeds supporting the Keene Community Kitchen.

A fall trail event in Harvard on October 25, 2026 featuring a 5K through orchard and woods plus a 1 mile kids fun run, with age divisions, awards, shirts, and proceeds benefiting the Harvard Conservation Trust.

Holistic Hustle in Kennebunkport features a timed 5K, a trail 10K and a kids half mile fun run at Emmons Preserve on October 31, 2026. The community fundraiser includes music, family activities, finishers medals and a raffle.

A costumed 5K trail run on October 31 2026 at Wells Reserve at Laudholm. Timed course with water stations and awards, with proceeds supporting coastal conservation and restoration.

Hugs From Vets Trail 10Kish in Henniker, New Hampshire on November 1 features a mixed trail and country road course and raises funds for American Legion Post 78. The field is limited to 150 participants and awards are given to overall and a..

The Hamsterwheel in New Boston, NH features timed 6, 12, 24 and 30 hour events on a scenic 4.0 mile loop along the New Boston Rail Trail, with chip timing, a central aid station, team entries, and buckle awards for 100 miles.

A November trail festival at Willowdale State Forest in Ipswich offering multiple looped distances from a 10K to 100K, a Cider Donut Mile, and a flagged 0.5‑mile youth run, with cupless aid stations and fundraising for local land trusts.