Trail Running calendar near Windham 2026-2027

A community fundraising 5K on Legacy Park's cross country trails with professional timing, post-run food and local beer and wine tasting for registrants 21 and over.

A three day 75 mile stage race around Lake Sunapee and a 50K on the SRKG Greenway featuring technical trails, significant elevation gain, and organized overnight camping.

The event is cancelled. It had been planned as a 10K ruck obstacle course at Pineland Farms in New Gloucester, Maine, featuring The Crucible with 20+ obstacles and prize rules requiring participants to ruck the full course with a pack.

The 15th Annual 5k Race to the Ledges in Concord, NH on August 8, 2026 features a short road and trail course and includes post-race brunch boxes to take away. Registration includes an adult 5 km entry and a free kids 5 km for ages 6 and un..

A community 5 km run in Derry, New Hampshire on August 8, 2026, with adult and kids categories and online registration closing August 7, 2026.

A 4.5 miles trail race on Frye Island on 08/08/2026 that starts and finishes at the Community Center and loops around the island through wooded trails. Registration opens 07/10/2026 and the fee is $10.

The Trust Trail Fest will take place in Kennebunkport on Sunday 9 August 2026. You can run between 5 and 10 kilometers.

A rugged 12 mile single track loop at Bradbury Mountain State Park, part of a small series and capped at 160 runners.

Multi-distance mountain trail event near Waterville Valley offering 108 mile, 58 mile and 20 mile courses across the White Mountain National Forest with significant elevation gain.

A 5K trail race at Wanakee in Meredith, NH on August 15, 2026 featuring wooded hills, granite trail sections, views from Look Out Point and a postrace Homecoming BBQ.

Trail race in Falmouth Maine offering 13 mile, marathon and 50K options on technical single track loops through Lowell Preserve and North Falmouth.

Third annual PRHS XC Alumni Race in Minot, Maine on August 22, 2026 features a 5K, a kids fun run, a barbecue and a kickball game.

A trail ultramarathon at Prospect Acres Ranch where runners complete repeated 2.2 mile laps in 2, 4, or 8 hour formats. Field camping is available Friday evening and registration is $40 with proceeds supporting future events.

A charity event at Medomak Valley High School with an untimed 1 mile walk, a 5K trail race, and a virtual 5K, with proceeds benefiting Boston Children’s Hospital.

Waterville Valley trail races on August 29 2026 offering 50K, 23K, 4 mile and 1 mile events with aid stations, a cupless policy, and required gear for the ultra.

A community race day at Cumberland Fairgrounds with a farmer’s market and music. Events include mile races, a kids 200 meter gallop and an open 5k that finishes on the horse track.

Trail races at Five Fields Farm in Bridgton ME featuring a three lap 50K figure 8 and a rugged 10K with steep, technical terrain and multiple aid stations.

A weekly fall trail running and walking series at Great Glen Trails in Gorham, NH from Sep 3 to Oct 8, 2026. Choose from 5 km, 3 km or 1.5 km courses; dogs on leash are welcome and one-time entries are available on-site.

Test your endurance at Pineland Farms in Maine with this backyard ultra trail race. Run a 4.2 mile loop through pristine wooded trails and see how many laps you can complete in this last person standing format.

Experience a flat and non technical trail race at Cherry Hill Farm in Gorham Maine. Choose between 50k 25k or 10k distances consisting of multiple loops around the scenic farm property.