Trail Running calendar near Greenwood 2026-2027

Big Brad Ultras at Bradbury Mountain State Park offers 25K and 50K options on a 15.5 mile single track loop. The course features technical terrain, multiple aid stations, drop bag access, and significant elevation gain.

The 12th Annual Skyline Farm 5K Trail Run & Walk on September 13, 2026 offers a scenic course through fields, hills and woods, a free Kids' 1K with prizes, post-event food and music, and awards including gift certificates and pies.

A remote, unmarked mountain event in Stark New Hampshire offering 50 Mile, 25 Mile, and 25K routes along the Kilkenny Ridge Trail. Runners navigate with provided GPS tracks, use limited backcountry aid, and must carry mandatory safety gear.

A 5K trail race at Loon Mountain on September 20, 2026, as part of the 51st NH Highland Games, with 800 ft of elevation gain across dirt trails, service roads and ski trails. Registration includes a race shirt and festival admission.

Pair up for a three hour endurance relay on a two mile loop of trails and fields. Alternate laps with your partner to accumulate the maximum distance possible in this team based challenge.

A traditional up and down mountain race in Waterville Valley, NH on September 20, 2026 covering about 7 miles with 3000 feet of ascent; youth entry is available and day of registration is offered.

One day across five Westmore peaks covering up to 26 miles and about 6142 feet of climb, with shuttle drop offs, staffed water and rest stations, limited entries to protect trails, and post-hike services at the NorthWoods campus.

A community trail festival in Arundel, Maine offering 5k, 10k and half marathon distances on the ACT and Eastern Trail, with participant shirts and medals, a free kids' bike race, live music, and food.

A looped trail ultra at Wolfe's Neck Farm in Freeport, ME, on a just over 5 mile dirt loop with stairs, bridges, and about 570 feet of gain per loop. Distances include 50 mile, 30 mile, and 10 mile options.

A 21k trail race on Pleasant Mountain in Bridgton, Maine on September 27, 2026. The route includes steep climbs, technical single track, one aid station, and a postrace gathering with food, beer for 21 plus, and live music.

Marathon Mont-Hereford on 27 September 2026 in East Hereford QC features trail races from 1 km to the marathon, a relay and a children's race. The event is listed with ITRA as 1 point and 4 mountain points.

An ultramarathon in Center Conway NH using the Last Person Standing format on a 3.5 mile loop of forest singletrack, trails, fields, and logging roads with about 250 feet of gain per lap. Camping is available the night before.

A 25 kilometer trail race at the Edwin L. Smith Preserve in Kennebunkport on October 3, 2026, with proceeds supporting the Kennebunkport Conservation Trust. Registration is capped at 100 and a shirt-included cutoff is on September 5.

Mile for Mentoring is a one mile community event in Gilford, NH on October 4, 2026, with adult and youth categories and a free entry for children under 12. Early registrants before September 16 receive a complimentary race shirt.

A trail ultra on Wright's Mountain in Bradford, Vermont on October 10-11, 2026 offering 30 hour, 12 hour and a 10K loop. The course mixes runnable sections with steep, rocky climbs and includes themed tarot card and milestone awards.

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 mixed human powered 100k in Norway, Maine combining 25 km of trail running with 75 km of biking across six preserves. Solo and duo options are available and proceeds benefit TruStrength Tomorrow and Western Foothill Land Trust.

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.

Trail races at East Windham Conservation Area in Windham, ME. The 50k is five 6.5 mile loops and the 10k is one loop, each loop with roughly 900 ft elevation and two aid stations offering snacks, water and electrolytes.

A looped endurance walk on Burke Mountain in East Burke, VT on October 25, 2026 offering 7, 14, 21, and 28 mile options across single-track, ridgelines, and ski trails. Options include weighted rucks, timed results, aid stations, and commem..