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
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.
Somers Thanksgiving Turkey Trot in Somers, NY features a 5K trail race and a 1 Mile fun run with age-group awards, shirts, medals, and packet pickup.
A community Thanksgiving run at Darien High School featuring a 5K and 1-mile walk/run, with music, food, and proceeds benefiting The Depot youth center.
A trail 5K at Bethpage State Park on November 28, 2026 offering in-person and virtual options, a free kiddie dash, race shirts and post-race refreshments.
A trail 5K at Belmont Lake State Park on November 29, 2026 with cash prizes from a raffle that awards 50% of net proceeds to present participants.
December 2026
Test your endurance at Sleeping Giant State Park by completing as many 3.3 mile loops as possible in 4 or 8 hours on the scenic Tower Trail.
A backyard ultra at Blydenburgh County Park: runners repeat a 4.167 mile loop each hour until one completes the final loop; proceeds support Long Island trail maintenance.
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.
Experience an exclusive trail run through the scenic Roosevelt Forest in Stratford. This 5K event features a natural off-road course limited to a small group of participants and includes custom finisher medallions.
An eight hour looped run at Lake Wintergreen in Hamden CT with 1.6 mile laps, one aid station, provided food and a 50 runner limit; proceeds benefit Doctors Without Borders.
March 2027
Trail events at Sunken Meadow State Park on a roughly 1.4 mile loop with one hour and three hour formats awarding titles for greatest distance covered.
Six hour timed trail event at Roosevelt Forest in Stratford CT with a 2.3 mile loop, a 50K option, limited field and awards for top mileage.
A 5K trail run and free kiddie fun run at Bethpage State Park with a good luck shirt, age group awards, refreshments, and a virtual participation option.
April 2027
A trail 5K at Bethpage State Park with a free kiddie run, virtual option, on-course refreshments, and proceeds to the Never Stop Running Foundation.
A community trail event in Cross River, NY featuring a 5k trail race, a 4k walk on the same trails, and a 200 meter kids dash on the contest track.
A 5K trail run and walk at Blydenburgh County Park supporting Last Chance Animal Rescue, with mixed trail surfaces, onsite refreshments and a dog friendly park.
Point-to-point trail runs of 50K and 25K across the Suffolk County Greenbelt Trail, finishing at Heckscher State Park on April 17, 2027.
Youth trail run at Katonah Memorial Park for ages 4 to 16 with 0.5 mile and 1 mile options; registration opens January 31, 2027.