Fairfield
Trail Running Calendar near Fairfield 2026-2027
Explore the top trail runs near Fairfield for 2026-2027! We've gathered 44 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A family friendly, obstacle filled beach 5k in Stratford that raises funds for Sterling Community Center while supporting individual and team fundraising.
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 six-hour timed run and relay at Belmont Lake State Park where individuals and teams cover as many 1.50 mile loops as possible, with awards and commemorative apparel.
October 2026
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.
Multi-day trail event in Rocky Point NY on a 10.48 mile loop used for distances from 10 to 150 miles, with two aid stations and crew support.
A timed 5K and accessible short run and walk at private Gemstone Farm in Wilton, CT with race shirt, post-race food, music, and support for The Prospector's mission.
A scenic 5K through the carriage roads of Rockefeller State Park Preserve with hilly terrain, Swan Lake views, awards, t shirts and proceeds supporting carriage road maintenance.
Trail 5K and free kiddie dash at Blydenburgh County Park on October 11, 2026 with a virtual option, finisher tee, shaded trails, and postrace refreshments.
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.
November 2026
Timed trail running on a 4 mile loop at Gurski Farm in Brookfield CT with 8 hour and 4 hour options plus a new 5K Canicross for 2026.
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.
A community 5K at Belmont Lake State Park on November 8, 2026 with in-person and virtual options, family activities, postrace refreshments, and proceeds supporting the Never Stop Running Foundation.
Championship cross-country 8K at Bethpage State Park on November 8, 2026, for Open, Masters and Para Athletic categories with age-group and team awards.
A family-friendly trail 5K at Bethpage State Park on November 14, 2026, offering in-person and virtual options, refreshments, finisher photos, and a free kids dash.
An inaugural backyard ultra at Cranbury Park where runners repeat a 4.167 mile loop each hour until one runner remains, with crew access and central aid near the corral.
Inaugural Estella's Memorial 5K in Yaphank is a fundraiser for the Lustgarten Foundation held on a flat loop trail at the Suffolk County Farm and Education Center.
Trail race at Tarrywile Park offering Marathon, Half Marathon and 10K on a loop course with roughly 3K of elevation and technical single-track.
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.
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 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.