Trail Running calendar near Great Barrington 2026-2027

Experience a 5K cross country run or walk through the mowed trails of Peach Hill Park. Reach the highest point in Poughkeepsie for panoramic views and enjoy post race snacks and awards.

Rise of the Obstacles in Wallkill NY is a two-day outdoor OCR event with a 100 m sprint, a two-lap endurance course, and kids' 50 m and 1 km races, featuring obstacle builds, finisher medals, and age-group awards.

Test your limits at this multi day vertical endurance series at Mohawk Mountain. Choose from seven elevation based challenges ranging from 12 to 84 hours as an individual or part of a flexible relay team.

Point to point trail ultramarathon along the New England Trail with 112 mile and 50 mile options through Connecticut. Entrants must donate to the Connecticut Forest and Park Association and arrange their own crew and navigation support.

Experience a timed 5K trail run or walk through the scenic woods and fields of the Van Vleck Farm and Nature Sanctuary. Enjoy live music and food trucks at this annual community event in Woodbury.

A 12 hour trail running festival in Moreau, NY on a *3.8 mile* loop featuring the staircase of death, steep climb and descent. Options include solo runs, relay teams with flexible lap order, a six hour category, and a Fun Run of 1 to 3 laps..

Paired 5K paved loop and 10K mountain trail at Rockland Lake State Park in Valley Cottage, NY. The 5K is a flat, fully accessible lake loop; the 10K climbs about 1,300 ft on rocky, steep terrain and includes one aid station.

A mountain running event in Roxbury, NY on June 7, 2026 featuring a 6.5 mile race with 3,500 feet elevation and a 5k with steep early gain and a downhill finish. Awards go to the top three men and women in each race.

Trail races at Ward Pound Ridge Reservation on June 7, 2026 include a half marathon and a 10K that pass the summit where the historic fire tower is being reconstructed. Proceeds support the Friends of the Fire Tower within the Westchester P..

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.

Experience a 5K trail and obstacle run featuring 24 challenges across a 400 acre campus in Wallingford. This inclusive community event supports adaptive sports programs through a mix of wooded trails and open fields.

Experience a scenic evening run on a flat paved loop around Rockland Lake. This chip timed half marathon features sunset views, frequent aid stations, and custom finisher medals only 45 minutes north of NYC.

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..

Trail races at Mansfield Hollow State Park include a roughly 15.7 mile out and back on the Nipmuck Trail and a new 5K single track loop; proceeds benefit Connecticut trail stewardship and the event is organized by the Shenipsit Striders.

A community 5K trail run, walk and hike in Eisenhower Park Milford on June 7, 2026 supporting the Milford Rotary and the Beth El Center. The course uses a high school cross country route with mostly flat sections and some rolling hills.

Manitou’s Revenge is a 53 mile ultramarathon across the Catskill Mountains from Windham to Phoenicia, New York. The route features about 15,000 ft of climbing, rocky remote terrain, long gaps between aid stations, and progressively harder s..

Celebrate the switch to summer with a trail race through the landscape of Hebron Connecticut. Choose between three different distances for a run through the woods during the solstice.

Test your endurance at Elka Park with this 14.5 mile weighted event. Participants navigate over 5,000 feet of elevation gain while carrying a 20 pound pack through the New York landscape.

A lap-based 100-mile trail event at Roosevelt Forest in Stratford, CT, with a 33-hour cutoff and a field limited to 50 runners. The course features New England single and double track, a single pavilion aid station, and pacer rules.

Experience an obstacle course weekend at a lush Massachusetts farm featuring rolling hills and mud. Choose from 5k and 10k races or the kids division with onsite farm treats and a local brewery.