Trail Running calendar near Brattleboro 2026-2027

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.

On May 31, 2026 at Ice House Park in Woburn, MA the second annual Live Free Fun Run and Festival pairs a scenic *2.5 mile* off-road run or walk with a community festival. The festival features food trucks, a DJ, activities and tables from l..

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.

A point to point trail event on the New England Trail offering 112 mile and 50 mile options. Self supported with crew, navigation by blue blazes, technical traprock terrain and typical finish windows of 30 to 45 hours.

A trail festival on a 3.8 mile loop featuring a rugged staircase that climbs over 800 feet in less than a mile. Runners can compete solo, join a relay team with flexible lap orders, or take part in a relaxed 1 to 3 lap Fun Run.

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. Hosts the 2026 USATF and Collegiate Mountain Running Championships and offers $30,000 in cash prizes.

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 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..

A trail festival at Norbrook Farm Brewery with running races, a run and bike duathlon, and mountain bike events on farm road and single track trails. Participants 21 and over receive one free beer ticket and there are finisher medals and aw..

A trail event in Dunstable, MA supporting the Humane Society for Greater Nashua, featuring a marked 5-mile loop with nearly 600 ft of elevation gain per lap and an optional 6-hour format for repeated laps.

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.

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.

A trail 5K and 10K at Pleasant Valley Wildlife Sanctuary on June 13 featuring mixed single-track and carriage-road terrain, water stations, finish-line food and music, and proceeds supporting local conservation.

Trail races at Mansfield Hollow State Park: a roughly 15.7 mile out and back on the Nipmuck Trail and a new 5K trail loop. Proceeds support Connecticut trail stewardship groups.

A loop trail run at Lawson Lake Park on June 20, 2026, featuring a 1.25 mile course with lake and creek views. Options include 2.5M, 5M, a one-hour format, and team entries; awards and a meal ticket are included.

Part of the Grit Series, this Dublin NH trail event offers a 10K and a half marathon with substantial elevation gain and views of Mount Monadnock. Registration runs from May 3 to June 6, 2026.

A loop-format trail event in Adams, MA where runners choose one, two, or three loops on machine and hand-built singletrack. Proceeds support Thunderbolt Ski Runners' stewardship of trails around Greylock Glen and Mount Greylock.