Trail Running calendar near Windham 2026-2027

The Windham Woods School Thankful Trails 5K will take place in Windham on Saturday 14 November 2026. You can run 5 kilometers.

A community memorial run in Tyngsboro, MA with a 1.5-mile walk and two 5K options, raising funds for a school scholar/athlete award and science scholarships while maintaining a tradition of food donations.

A Last Person Standing mountain event with hourly 2.25 mile laps that climb about 1,209 feet each. Aid, hot food, camping, elevation milestone prizes, and awards are provided; conditions may include cold, snow, or ice.

Enjoy a festive four mile trail race through the wide paths of Mine Falls Park. All proceeds from the run and raffle support residential and educational programs at the Nashua Childrens Home.

A trail running event at Middlesex Fells Reservation with **8 mile**, **32 mile**, and **40 mile** loop options on the white blazed Skyline Trail. The course is technical and minimally marked, cupless with two aid stations and specific cour..

Celebrate the twentieth anniversary of this unique cross country race held at the Mount Hood Golf Club. Choose between a competitive three and a half mile run or a festive two mile walk through hilly terrain.

Experience a winter trail challenge at Hale Education featuring 15 mile and 30 hour options. Navigate three unique loops through the Massachusetts woods while testing your endurance and self reliance in cold weather conditions.

Experience the US Snowshoe Nationals in Concord New Hampshire. This winter event features 5k and 10k races on a flat and fast course through open fields and singletrack trails.

Trail races at Monastery Trails in Cumberland, RI on March 14, 2027 offer distances from a 1 mile kids run to a 100K 12 hour ultra. Team ultra entries and a multilap 5 hour option are available and all finishers receive a medal.

Trail races and a 1 mile Color Run in Salisbury on March 27, 2027, featuring 10K, 5K and a non timed color run, with proceeds supporting Salisbury Parks and Recreation.

Trail race in Union, CT on the Nipmuck Trail covering about 16 miles through Yale-Myers Forest. Organized by Shenipsit Striders with limited aid stations and parking; proceeds support local trail stewardship.

A 123.2 mile point to point ultramarathon across Connecticut from East Thompson to Southport with mixed trail and road terrain, aid stations and medical support, a 36 hour limit, plus 100K and relay options.

An obstacle course race in Cumberland, Rhode Island featuring a 3.2 miles course with about 1,000 feet elevation, multiple wave formats including elite and age group competition, multilap sessions, and a 12 hours ultra option.

The TARC Spring Classic takes place April 24, 2027 in Jericho Town Forest, Weston, MA, with 10K, half marathon, marathon and 50K looped trail options, a single aid station, marked course, and a cupless race format.

A trail running event on the Wapack Trail in Ashburnham Massachusetts with 21.5 mile, 43 mile, and 50 mile options across rocky, technical terrain with aid stations, drop bag support, and a manual timing system.

A looped hill endurance event in Cumberland Rhode Island where participants run or hike as many laps as possible within a 12 hour period. The top male and female who cover the greatest distance are named King and Queen of the Hill.

The inaugural F.I.T. 50k in Cumberland, Rhode Island is a 50k trail ultramarathon with equal parts smooth non technical and moderately technical terrain. The event includes a generous cutoff time and a $65 registration fee.

The New England Spartan Event Weekend will take place in Barre from Saturday 26 June 2027 to Sunday 27 June 2027. You can run between 5 and 10 kilometers.