New Canaan
Trail Running Calendar near New Canaan 2026-2027
Explore the top trail runs near New Canaan for 2026-2027! We've gathered 46 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
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.
Community 5K and untimed fun run on November 7, 2026 at Sachem North High School with T-shirts, live results, finish line photos, and age group awards.
A 46th annual 4K cross country at the VA Golf Course in Northport with proceeds supporting hospitalized and homeless veterans; includes a free short fun run and a virtual 4K.
Timed laps at New Canaan High School Track where adults run for 14 minutes and 48 seconds and kids run one 400 m lap, with proceeds supporting the Ram Council Foundation.
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.
Cross country championship 8K at Bethpage State Park on November 8, 2026, for Open, Masters and Para Athletic divisions with age-group and team awards.
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.
A scenic second-annual 5K at the New York Botanical Garden on November 8, 2026, combining road and trail sections with post-run festivities and garden views.
Family friendly 5K trail run and walk at Bethpage State Park on November 14, 2026, with a virtual option, a free kiddie dash, and post race refreshments.
Experience technical single track trails and significant elevation gain at Tarrywile Park with marathon, half marathon, and 10k race options in Danbury.
Scored NYRR cross country 5K at Van Cortlandt Park on November 15, 2026, with wooded trails, bag check, on-site awards, and runner tracking.
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.
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.
A farm based 5K trail run plus a kids fun run for ages 6 and under in Yorktown Heights supporting Friends of Hilltop Hanover Farm.
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.
Charity 5K and timed 1 mile walk/run at Darien High School on November 27, 2026 supporting The Depot, with family activities and bib pickup options.
5K trail run and virtual 5K at Bethpage State Park on November 28, 2026 with a free kiddie dash and proceeds supporting the Never Stop Running Foundation.
A revived 9 mile cross-country race in Van Cortlandt Park covering three loops of the park’s XC course with awards, commemorative buffs, and a post-race pub gathering.
December 2026
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.