Kent
Trail Running Calendar near Kent 2026-2027
Explore the top trail runs near Kent for 2026-2027! We've gathered 15 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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.
A charity 5K on the scenic trails at Norbrook Farm Brewery in Colebrook CT supporting the Lymphoma Research Foundation with local beer available after the run.
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
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 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.
A community 5K and a 1-mile kids run at Sargent Elementary in Beacon, NY, with a food drive, live DJ, and refreshments.
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.
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.
December 2026
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.
May 2027
A technical trail race in Beacon NY with a half and full marathon featuring heavy elevation gain, exposed climbs, aid stations, and strict aid station support rules.
June 2027
Multi-day vertical trail endurance series at Mohawk Mountain, June 2–6, 2027, with Solo and team FlexRelay options and events from 12 to 84 hours.
July 2027
A roughly 5 miles trail run through varied terrain at Bowdoin Park in Wappingers Falls, with a 150 runner cap and awards for overall top finishers.