Trail Running calendar near Windsor 2026-2027

Trail races in Keene, NH on a revised, technical course where runners choose how many 12.5k laps to run. Natural single track and jeep roads, cupless aid stations, parking at Fuller Elementary School, and drumstick awards.

Mine Hill Half Marathon is a 13.1 mile road race in Roxbury, Connecticut, with start and finish at Mine Hill Distillery. The course passes farms, fields and scenic vistas and includes a post-race gathering at the distillery.

A Memorial Day Weekend inaugural *5k* trail run through Groton's General Field on May 24, 2026. The event supports Operation Delta Dog, which rescues and trains service dogs for veterans.

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.

Test your endurance at the Ascutney Mountain Run in Vermont. This 3.7 mile uphill race climbs 2,300 vertical feet along a paved auto road to a scenic mountain summit finish.

A running event in Granville on May 30, 2026: a relatively flat 5k along the rail trail finishing on the footbridge over the Mettowee, plus a kids 1k. Registration opens March 26; 5k fee $25, kids run free.

A choose your own adventure trail event at Chesterfield Gorge Reservation on a rolling jeep road alongside the river. Multiple ultra and shorter distances are offered, with a 30 hour window for ultras, water and manned aid stations, and non..

Multi-day elevation based endurance events at Mohawk Mountain in Connecticut, June 4 to 7, 2026. Solo, Trail Buddy and Trail Family formats cover timed events from a 12-hour 15-mile option up to 84-hour 152+ miles with large elevation gain.

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..

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.

A two lap mountain race at Mount Sunapee in New Hampshire covering about 9.3 miles and 3,300 feet of ascent, hosting the 2026 USATF Mountain Running Championships with $30,000 in cash prizes and concurrent collegiate and high school champio..

A community event at Stanley Park on June 7, 2026 featuring a 5K trail run or a one mile accessible route. Proceeds support renal medullary carcinoma awareness and related programs.

A flat, non technical trail 5K at Schodack Island State Park on June 7, 2026, with kids races, post race music and a BBQ. Entry fees rise by registration period and kids races cost five dollars each.

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 day of trail running and mountain biking at the Norbrook Farm Brewery Trail Festival. Enjoy multiple race distances, local food trucks, and rewards at this scenic Connecticut brewery.

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.

Trail race options of 50k, 30k and 10k around Edge Hill Conservation Area in Ashfield Massachusetts, run on single track and dirt roads. The event partners with Franklin Land Trust and supports habitat restoration and land conservation.

A trail race in Newport, New Hampshire on June 13, 2026 offering 6 and 3 mile routes through rocky, rooty, hilly forest trails. Proceeds support Newport Recreation and town forest trails and awards are pure New Hampshire maple syrup.