Trail Running calendar near Somers 2026-2027

A stadium stair climb at Gillette Stadium on October 25, 2026 featuring timed waves, music and big screen highlights. Net proceeds benefit Home for Our Troops and a spectator option is listed.

Trail races at Red Wing Recreation Area in Lagrangeville, NY featuring 100k, 50k and 10k looped courses with significant elevation, on-course aid, and finisher awards.

Experience a unique timed trail event at Gurski Farm featuring a four mile loop of rolling farm trails and single track. Choose between eight hour, four hour, or 5K options in a community focused environment.

A 10K trail race in Penwood State Park featuring technical single track on the Metacomet Trail and rocky runnable terrain. No aid stations so runners must carry hydration for 6.2 miles; proceeds partly support NAMI.

A two day obstacle event at Fenway Park in Boston featuring a Stadion 5K with 20 obstacles, a kids race, and spectator access. The course uses stadium features including the Green Monster, clubhouse, and home plate.

A multi-duration timed trail event in New Boston, NH on a 4.0 mile marked loop along the Piscataquog River. Options include solo and relay times, chipped bib timing, central aid station services, team entries, and 100 mile buckles.

A last runner standing backyard ultra on private farmland in Winchendon with a 4.1666 mile loop. The event also offers 6 hour, 12 hour and 24 hour timed options plus a standalone fastest lap competition.

A looped 3.1-mile trail course at White Barn Farm in Wrentham MA with distances from 5K to 50K and a central aid station. Runners complete repeatable laps and may stop after any finished loop.

A trail event at Ward Pound Ridge Reservation featuring a marked 10k race and a monthlong Raven 100k November Challenge. The course includes rocky climbs, ridgeline trails and a water stop near the Fire Tower climb.

A 5k chip-timed run/walk at Stonington Vineyards on November 8, 2026 featuring a two-lap cross country route through the vines. Registration includes a shirt, collapsible wine glass, finisher medal and a pour of wine.

Trail races in Upton State Forest offer 10.5K and half marathon options over technical, hilly single track and forest roads. The event has a 250 runner cap and aid stations spaced roughly every three miles.

A family friendly run and walk at West Thompson Dam on November 8, 2026 featuring a timed 5K trail run, a 3K untimed walk and a free kids 1/4 mile run; proceeds support local trails, parks and a food pantry.

A 6 hour timed trail race on a 5K loop at Wright Locke Farm in Winchester Massachusetts, featuring rocky rolling singletrack, a barn aid station in a cupless format, and provisions for adaptive athletes and youth discounts.

Trail races at Tarrywile Park in Danbury, CT offering 10K, half marathon and marathon options on technical single track; the half uses a loop with close to 3K of elevation and a cupless race policy.

A November trail race at Burlingame State Park offering 4 mile and 8 mile courses on dirt trails and roads, a required orange garment mandate, post-race food, and age group awards for both distances.

Experience a magical 13.1 mile trail race through the rolling hills of Roosevelt Forest. Complete eight loops of a wooded course while supporting a children's book drive in this unique costume friendly event.

A community memorial run in Tyngsboro, MA with a 1.5-mile walk and two 5K options, raising funds for a school scholar/athlete award and science scholarships while maintaining a tradition of food donations.

Trail races at YMCA Camp Sloper on a roughly two-mile loop: a 400 minute time-limit event with loop counting and a four mile two-lap race, chip timing, a single aid station, cupless policy, and proceeds to local organizations.

Enjoy a festive four mile trail race through the wide paths of Mine Falls Park. All proceeds from the run and raffle support residential and educational programs at the Nashua Childrens Home.

A community Thanksgiving trail event on 11/26/2026 at Mill Pond Way Trail with a 3.5 mile run or walk, chip timing, post race yoga for participants, free water and snacks, and proceeds benefiting endometriosis research.