Trail Running calendar near Windsor 2026-2027

Join a small group trail running camp in the Catskill mountains for a weekend of guided coaching. The program includes long runs on technical terrain and mental performance sessions to prepare for local mountain races. All skill levels are..

A lap-based trail race in Keene NH using a 12.5 km loop with options up to 50 km, technical wooded terrain, aid stations, and a cupless policy requiring personal hydration gear.

A road half marathon in Roxbury, Connecticut on May 24, 2026 that features mixed pavement and dirt sections, notable climbs including a 250 foot gain near the halfway point, and a post race celebration at Mine Hill Distillery.

A multi day endurance series at Mohawk Mountain in Connecticut offering solo and team trail events from 15 to 152+ miles with timed formats up to 84 hours. Tenting, support stations, and personalized bibs and medals are provided.

A point-to-point ultramarathon on the New England Trail offering 112-mile and 50-mile options to Guilford. Entrants must make a donation to the Connecticut Forest and Parks Association and arrange their own crew and navigation.

A five mile fun run along the Cheshire Rail Trail from the Fitzwilliam Railroad Depot to the restored Troy Depot, with a short children's loop and food and festivities at both depots. The event raises funds for local historical societies.

A unique trail festival centered on a rugged 3.8-mile loop featuring the infamous "staircase of death." Run solo, join a flexible relay team, or take on the casual Fun Run over a 12-hour period. Start when you like and enjoy the community a..

Plattekill Mountain Race on June 7, 2026 in Roxbury, NY features a 6.5 mile mountain race with 3500 ft of climbing and a steep 5k. Top three men and women will receive awards and finisher swag is planned.

A two-lap mountain race at Mount Sunapee on June 7, 2026, serving as the USATF National Classic Mountain Championship and the Collegiate Mountain Running National Championships. About 9.2 miles and roughly 3,250 feet of elevation gain.

This multi-sport festival at Norbrook Farm Brewery offers trail runs, a duathlon, and mountain bike races on scenic 5K and 5-mile loops. Participants enjoy local food and a post-race brewery celebration. Registration includes a finisher med..

Explore the hill towns of western Massachusetts on a mix of trails and dirt roads. Choose from a 50k, 30k, or 10k distance, with all proceeds supporting the Franklin Land Trust's conservation efforts at the scenic Edge Hill Conservation Are..

A trail running event at Mansfield Hollow State Park offering a 15.7 mile out-and-back on the Nipmuck Trail and a new 5K course entirely inside the park. Proceeds support Connecticut trail stewardship groups.

Manitou's Revenge is a 53 mile ultramarathon across the Catskills with about 15,000 ft of climbing, rocky and steep terrain, limited aid stations, and long self supported stretches between services.

Early morning trail run in Gay City State Park offering 3, 5 and 8 mile races. The 8 mile is part of the Blue Blazed and USATF CT MUT series and includes teams of three competing for prize money.

Twelve hour timed run on a 4.25 mile loop with about 500 feet of gain per loop in Hamden, CT. Options include marathon via six loops, 50K via eight loops, and a 50 mile target; proceeds support the Brooksvale Gift Fund.

Trail racing at Red Wing Recreation Area with 15K, 30K, and 60K options on a 15k loop featuring varied terrain, aid stations, lap support for 60K runners, and post race food and drinks.

Notchview Ultra in Windsor MA runs multiple timed events on a 1.9 mile loop with an on-course aid station, campsite options, and beneficiaries including the Trustees of Reservations and Baypath Humane Society.

A 5.5 mile trail race at Soapstone Mountain featuring six ascents and about 1500 feet of climbing. The route circles the mountain with multiple steep rocky sections, limited aid access, and a field limited to 50 runners due to parking.

An 8 hour timed track event at Clapp Park on a certified 0.355 mile dirt and cinder loop, featuring chip timing, trackside bottle drop aid, age division awards, a possible virtual option, and proceeds benefitting the AYJ Fund.

The Slate Valley Scramble will take place in Poultney on Saturday 8 August 2026. You can run between 8 and 13 miles.