Fairfield
Trail Running Calendar near Fairfield 2026-2027
Explore the top trail runs near Fairfield for 2026-2027! We've gathered 51 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.
A community 72nd anniversary event in Lake Ronkonkoma with a timed 5K run/walk and an untimed fun run on mixed pavement, grass and trail surfaces.
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.
A community 5K at Belmont Lake State Park on November 8, 2026 with in person and virtual options, a free kiddie dash, post race refreshments, and proceeds supporting NSRF.
USATF Long Island 8K Open and Masters Para Athletic XC Championships on November 8 2026 at Bethpage State Park Playground in Bethpage NY
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 family 5K trail run and virtual option at Bethpage State Park on November 14, 2026 with a free kiddie dash, post-race refreshments, and proceeds supporting the Never Stop Running Foundation.
An inaugural backyard ultra at Cranbury Park where runners repeat a 4.167 mile loop each hour until only one runner completes a lap.
A farm-based memorial 5K and kids fun run on 11/14/2026 at the Suffolk County Farm and Education Center raising funds for pancreatic cancer research.
Experience technical single track trails and significant elevation gain at Tarrywile Park with marathon, half marathon, and 10k race options in Danbury.
Trail half marathon and 5 mile at Brookhaven State Park on Nov 15, 2026, on single track and fire trails with awards, cash prizes, and finisher medals.
Six hour timed run and relay at Belmont Lake State Park on November 15, 2026 featuring individual and team entries on a 2.50 mile loop with post event food and awards.
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.
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.