Trail Running calendar near Chester 2026-2027

A chip timed 5k at Ledge Rock Hill Winery in Lake George, NY, on a cross country style out and back course. Race swag includes a T shirt, a shatterproof collapsible wine glass and a medal, with age group awards and charity partner Nik's Wis..

Infinitus in Ripton, Vermont runs May 21 to 31, 2026 and offers trail races from a 9 mile option up to 250 mile and multi marathon formats. The course uses two loops and on site camping is available for a small cash fee.

Trail races in Keene, NH using a 12.5K loop that can be repeated for 12.5K, 25K, 37.5K, or 50K. The course is technical single track and old jeep roads with aid stations, drop bag access, and portable toilets.

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.

A four race 5 km trail series at Cole's Woods in Glens Falls across Tuesdays in May, with a 20 km challenge for those who complete all four events. Entry fees, T shirt allocation, awards and proceeds benefiting the Glens Falls Youth Center..

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.

A forest trail 5K in Montpelier, VT on May 30, 2026 featuring mostly single track, technical roots and rocks, and about 500 feet of elevation gain. The marked course runs through North Branch trails and is part of the local race series.

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 23K mountain trail race in Tamworth NH with roughly 4,800 feet of climbing, a technical loop over the 3,478 foot summit of Mount Chocorua, mandatory mountain safety gear, and inclusion in the White Mountain Endurance Cup.

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 trail event in Bradford, Vermont on June 6, 2026 featuring a 5K that climbs to Wrights Mountain summit and a 1.5 mile fun run for ages 13 and under. Proceeds support the Friends of Wrights Mountain Fund.

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.

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 6.9 mile trail race at Cannon Mountain on June 13, 2026 with 3,080 ft of elevation gain and a 4,031 ft summit. The marked course includes steep ridge and ski-trail sections and is capped at 500 runners with a 2 hour summit cut off.

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 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 featuring 6 miles and 3 miles on rocky, rooty, hilly town forest trails; age and gender categories award Pure NH maple syrup to top three finishers and proceeds support local trails.