Roxbury
Trail Running Calendar near Roxbury 2026-2027
Explore the top trail runs near Roxbury for 2026-2027! We've gathered 35 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A 30 hour loop ultrarun in Roosevelt Forest CT on 2.5 mile laps offering distances to 100 miles with a finisher buckle and a single pavilion aid station.
A 5K trail run and an accessible short run/walk on private Gemstone Farm in Wilton, CT on 10/10/2026, with farm access, post-event food and entertainment, supporting The Prospector.
Trail races at Mohawk Mountain Ski Area in Cornwall, CT on October 11 with 5K, 10K, half and full marathon courses over ski slopes and Mohawk State Forest.
A 3.5 mile trail run and walk on the scenic, flat Mill Pond Trail at Woodtick Recreation in Wolcott CT on October 17, 2026. Tiered online registration is available and a post-event meal is included with registration.
Trail running at Muscoot Farm with a 5 mile race and two kids races on October 25, 2026 in Katonah, NY.
Trail ultramarathon weekend in Lagrangeville with 100k, 50k and 10k looped courses, UTMB Index status and continuous on-course aid.
November 2026
Experience a community-focused trail race featuring a 4 mile loop of rolling farm trails and single track with timed options, a 4 mile distance, and a 5K Canicross.
A trail 10k at Ward Pound Ridge Reservation on November 8, 2026 plus a monthlong November Raven 100k Challenge with a wooden finisher medallion.
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.
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 races at YMCA Camp Sloper with a 400-minute loop challenge and a 4-mile option on a marked, varied-surface course with aid station support.
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.
3.5 mile trail run and walk at Mill Pond Way Trail in Wolcott, CT with post-race yoga, chip timing, medals, and proceeds benefiting endometriosis research.
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.
Somers Thanksgiving Turkey Trot in Somers, NY features a 5K trail race and a 1 Mile fun run with age-group awards, shirts, medals, and packet pickup.
December 2026
Test your endurance at Sleeping Giant State Park by completing as many 3.3 mile loops as possible in 4 or 8 hours on the scenic Tower Trail.
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.