Trail Running calendar near Springfield 2026-2027

A dirt road 50k in Leyden, Massachusetts on May 16, 2026, with 4,200 feet of elevation change and a course that passes through forests, fields, and an 1870s covered bridge. Registration closes May 13 and there is no race-day entry.

A 5 km cross-country event at Canterbury Shaker Village on May 16, 2026 with in-person and virtual options. Online registration closes May 15 at 12:00 noon ET and the registration fee is $25.

A May race day on the Ashuwillticook Rail Trail offering a marathon, half, 8K and kids mile, with race shirts, finisher medals, aid stations, and proceeds supporting trail maintenance.

Trail running in Pittsfield State Park with 50K, 25K and a 5 mile course on single track and flowy forest trails. The event is organized by BURCS and benefits local animal rescue organizations.

A 50-mile point to point ultramarathon from Manchester to Mount Monadnock with about 6000 feet of gain over roads, dirt roads and trails. The course is GPX only with minimal markings, five aid stations, and a 125-runner cap.

Wason Pond Wrangler is an obstacle race on May 16, 2026 in Chester, New Hampshire, featuring a 5 km course run in multiple waves including a competitive wave. Online registration is closed and the event is limited to 800 participants.

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..

A 5K Fun Run at Strongwater Farm in Tewksbury on May 17, 2026 to raise funds for programs supporting people with mobility challenges. The trail course crosses corn fields and woods, with a shorter accessible route and family activities on s..

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.

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.