Fairfield
Trail Running Calendar near Fairfield 2026-2027
Explore the top trail runs near Fairfield for 2026-2027! We've gathered 50 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
May 2027
A nine hour timed trail ultra on a 2.2 mile loop through Roosevelt Forest in Stratford, CT. Entry is limited to 50 participants and awards go to the runners with the most miles by the race end.
A 5K run and walk at Bethpage State Park with live results, free finish line photos, soft trail terrain and awards for top overall finishers.
A 5K trail run and walk at Blydenburgh County Park with in-person and virtual options, refreshments, and proceeds benefiting the Never Stop Running Foundation.
A 5 mile trail race at Muscoot Farm on May 23, 2027 with two kids races on farm trails. The event is organized by Run the Farm Races and is sanctioned by USA Track and Field.
June 2027
Trail races at Ward Pound Ridge Reservation on June 6, 2027 include a half marathon and a 10k that pass the summit where the historic fire tower is being reconstructed. Proceeds support Friends of the Fire Tower for accessibility and educational impr..
August 2027
A scenic 2.5 mile trail run at Wildwood State Park in Wading River on August 7, 2027 with live results and free finish line photos.
A multi-day August 2027 event at Sacred Heart University with 90 minute stair climb and walk challenges plus a five day virtual step challenge supporting Homes for the Brave.
September 2027
Timed six-hour run and relay at Belmont Lake State Park on a 2.50 mile loop with individual and team competition, awards, commemorative apparel, and post-event food.
October 2027
A shaded trail 5K at Blydenburgh Park with a free kiddie dash, virtual participation, race tee, on-site refreshments and age-group recognition; proceeds benefit a running foundation.