Roxbury
Trail Running Calendar near Roxbury 2026-2027
Explore the top trail runs near Roxbury for 2026-2027! We've gathered 37 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A community trail event at Ives Farm featuring a 5K, an elementary school relay, a free Pumpkin Dash for young children, family activities, and free training sessions.
Test your endurance at the Pawling 24 Hour Trail Running Festival featuring multiple timed races on a scenic 1.68 mile loop in Lakeside Park.
Trail races in Ridgefield CT offering a single loop of about 4.25 miles or a double loop of about 8 miles through Hemlock Hills and Pine Mountain. The technical, rocky course starts and ends at the Lake Windwing ballfields.
A 5K trail run at Winding Trails in Farmington on the designated course around Walton Pond, with registration from February 20 to September 20 and a $35 fee; overall and age-group awards plus a prize for the first local finishers.
Experience a technical trail race through the Nassahegan State Forest and Devil’s Kitchen in Burlington, featuring 5K and 8K distances on the Blue-Blazed hiking trail system.
October 2026
A veteran-run series of elevation-based mountain endurance events at Mohawk Mountain CT and Amicalola Falls GA, offering seven solo and team formats from 12 to 84 hours.
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.
Experience a trail run through Mohawk Mountain Ski Area and Mohawk State Forest featuring steep climbs and scenic fall foliage across distances from 5 km to a full marathon.
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 event at Muscoot Farm in Katonah on October 25, 2026 featuring a 5 mile race and two kids races, with Farm Bucks and kids medals.
Test your endurance at Red Wing Recreation Area with a series of looped trail races ranging from 10k to 100k featuring significant elevation gain and constant support.
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.
Trail events at Ward Pound Ridge Reservation: a 10k trail race on November 8, 2026 and a month long Raven 100k Challenge with wooden finisher medallions.
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 in Southington CT with a 400 minute timed loop event and a four mile two lap race organized by CT Trailmixers.
Inaugural Stride for the Knights 5K at Southington High School on November 22, 2026, features wooded cross-country routes, a new track finish, and a Kid's Fun Run.