Trail Running calendar near Chesterfield 2026-2027

A four-race 5K trail series in Cole's Woods, Glens Falls, held Tuesdays in May. Runners who complete all four races form a 20K challenge and compete for overall awards and raffle prizes.

A weekly 5K trail series at DCR Robinson State Park in Agawam, MA, running Tuesdays from May 26 to August 25, 2026. The course uses rolling double wide and single track trails; onsite registration and a small weekly fee apply.

A 5K trail event on May 30, 2026 at Danvers YMCA Camp in Boxford with separate courses for runners and for walkers and waggers, pond and vernal pool scenery, prizes, post-race treats, and registration benefits.

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 ultra and trail event at Chesterfield Gorge with multiple distances, lap based 50k to 100mi options, a 30 hour window for ultras, and timed 33k and 11k races the following day.

The second annual Live Free Fun Run and Festival in Woburn features a scenic 2.5 mile off-road run or walk around Horn Pond. The festival includes food trucks, a DJ, kids activities and tables from over 25 local mental health and substance..

A family friendly Monday night trail series in Nashua offering 5K and 5-mile races plus virtual options, themed evenings with music and giveaways, and occasional frozen treats at the finish.

A weekly 5K cross-country trail series at Worthington Winery in Somers, Connecticut, held Wednesdays from June 3 to July 1, 2026. The course runs through backwoods and vineyard areas with views of ponds and a covered bridge.

Point-to-point trail events of 112 miles and 50 miles along the New England Trail in Connecticut. Self-navigation is required, crew support expected, and donations to the Connecticut Forest and Park Association are required for entry.

A 12-hour trail event in early June 2026 at Overlook Trailhead near Moreau beach featuring a 3.8-mile loop with a steep staircase climb. Participants can run solo, form relay teams, or enter a Fun Run of one to three laps.

A trail event on Wright's Mountain in Bradford, Vermont offering a 5K with an 850 foot climb and a 1.5 mile youth fun run. Proceeds support the Friends of Wrights Mountain Fund for forest maintenance.

A community running event on June 6, 2026 in Holliston with 5K, 10K, and a Kids Fun Run on the flat Holliston Rail Trail. Registration opens March 1; fees are $30 for the 5K and 10K and $5 for the kids run.

A two-lap mountain race at Mount Sunapee Resort on June 7, 2026, covering about 9.3 miles and 3,300 feet of climbing. The event hosts the 2026 USATF Mountain Running Championships and the Collegiate Mountain Running Nationals with cash priz..

Run for RMC on June 7, 2026 at Stanley Park in Westfield MA offers a 5K trail run and a 1 mile accessible route to raise awareness of renal medullary carcinoma and support 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 Fitzwilliam Depot to the restored Troy Depot on June 13, 2026. The day features food and festivities, a children's loop, return transport on request, and benefits local historical socie..

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.

A second annual trail event in Dunstable, Massachusetts offering a 5 mile loop or a six hour race of repeated 5 mile loops. The course follows an old railroad bed, an arched stone bridge, woods, peaks, and single track trails.

Trail races of 50k, 30k and 10k through western Massachusetts hill towns on single track and dirt roads, held in partnership with Franklin Land Trust and featuring aid stations, first aid and locally produced awards.