Roxbury
Trail Running Calendar near Roxbury 2026-2027
Explore the top trail runs near Roxbury for 2026-2027! We've gathered 29 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
Trail races at Tarrywile Park in Danbury offering Marathon, Half Marathon and 10K on a loop course with technical single-track, substantial elevation gain, and cupless aid stations.
A trail half marathon at Roosevelt Forest on November 21, 2026 featuring eight 1.64 mile loops, on-course aid, commemorative swag, and podium awards for top male and female finishers.
CT Trailmixers event at YMCA Camp Sloper offers a 400 minute loop style race and a 4 mile option, chip timed with on course aid and limited entries.
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 at Southington High School features a wooded cross-country course with a track finish, a kids fun run, and awards from Fleet Feet.
3.5 mile trail run and walk around Scoville Reservoir with chip timing, post-race yoga, medals, swag and age-group awards.
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.
Third annual 5K Reindeer Run/Walk on the Joel Barlow cross-country course in Redding, CT with festive attire encouraged and proceeds to the Class of 2029.
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.
An 8 hour loop event at Lake Wintergreen in Hamden CT with 1.6 mile loops, one aid station, on course snacks and a 50 runner limit. Proceeds support Doctors Without Borders.
March 2027
A 6 hour trail ultra at Roosevelt Forest in Stratford CT with a 2.3 mile loop, on-course food and hydration, a 50 person field, and podium awards for top men and women.
April 2027
A community trail event in Cross River, NY featuring a 5k trail race, a 4k walk on the same trails, and a 200 meter kids dash on the contest track.
Youth trail run at Katonah Memorial Park for ages 4 to 16 with 0.5 mile and 1 mile options; registration opens January 31, 2027.
A spring trail event in Cross River NY, Leatherman's Loop is a 10K lottery-entry race with a $58 fee that includes park entry.
May 2027