Roxbury
Trail Running Calendar near Roxbury 2026-2027
Explore the top trail runs near Roxbury for 2026-2027! We've gathered 34 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Trail event at Muscoot Farm on Oct 25, 2026 with a 5 mile race, two kids races, Farm Bucks and medals for young finishers.
Trail races at Red Wing Recreation Area Oct 31 to Nov 1 2026 offering 100k, 50k and 10k looped courses with aid stations and finisher medals.
November 2026
Timed trail running at Gurski Farm in Brookfield CT on a rolling four mile loop with 8 hour, 4 hour, and a new 5K canicross option.
A technical 10k trail race at Ward Pound Ridge Reservation with a parallel November Raven 100k Challenge offering badge-based achievements and a wooden finisher woodallion.
A 100 percent cross country 5K at White Memorial Foundation & Conservation Center in Litchfield with natural trail footing, a midcourse hill, on-site outhouses, and Sawmill Field parking.
Trail event at Alice Newton Street Park in Woodbridge CT offering a 4 mile trail run and a 2 mile woodland walk, with shirts, refreshments and awards.
Experience technical single track trails and significant elevation gain at Tarrywile Park with marathon, half marathon, and 10k race options in Danbury.
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.
Trail event at YMCA Camp Sloper offering a 400 minute timed loop race and a 4 mile two lap option on a flagged, roughly two mile trail course.
A memorial 5K run and walk on the cross country course in Danbury offering a chance for friends, family and teammates to gather and remember.
Inaugural Stride for the Knights 5K on November 22, 2026 at Southington High School features a wooded cross country course and a kids fun run.
Second annual Thanksgiving 3.5 mile trail run and walk around Scoville Reservoir in Wolcott CT supporting endometriosis research with post-race yoga and finisher medals.
A ninth annual charity 5K in Roxbury, Connecticut on November 26, 2026, with a 3.1 mile out-and-back course near Everett B. Hurlburt Community Park. Proceeds support local ambulance and scholarship funds and a food pantry collection.
Community Thanksgiving event at Somers High School with a 5K and 1-mile fun run, shirts, medals, age-group awards, and scheduled packet pickup days.
December 2026
Timed trail event at Sleeping Giant State Park with repeated 3.3 mile out and back laps on the Tower Trail and 4 hour or 8 hour options.
A 5 mile winter trail race at Mountain Lakes Park in North Salem NY with start and finish in the Yurt Village, a central firepit, and proceeds supporting park trail projects.
Experience an exclusive trail run through the scenic Roosevelt Forest in Stratford. This 5K event features a natural off-road course limited to a small group of participants and includes custom finisher medallions.
Eight hour loop event on 1.6 mile laps around Lake Wintergreen in Hamden CT with one aid station, food, a 50 runner limit and proceeds benefiting Doctors Without Borders.
March 2027
A six-hour trail ultra at Roosevelt Forest featuring a 2.3-mile loop with 191 feet of climb per lap, chip-timed laps, on-course aid and food, podium awards, medallions for over four hours, and a limited field supporting local charities.