Monroe
Trail Running Calendar near Monroe 2026-2027
Explore the top trail runs near Monroe for 2026-2027! We've gathered 32 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
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.
December 2026
Timed up and back trail event at Sleeping Giant State Park with four hour and eight hour options and 3.3 mile laps to the Observation Tower.
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.
March 2027
A six hour trail ultra at Roosevelt Forest in Stratford CT on a 2.3 mile loop with roots, rocks and rolling hills; field limited to 50 participants.
April 2027
A community trail event in Cross River, NY featuring a hilly wooded 5K, a 4K walk through the main trail, and a 200 m kids dash on the contest track. Registration opens 8/24/2026 with limited pre-registration t-shirt incentives.
A USATF sanctioned 10K trail race in Cross River NY on April 25, 2027, with entry via lottery and a $58 registration fee that includes park entry.
May 2027
Camp Mountain Laurel offers a family color run plus a 5K trail run and 5K trail walk at Hamden/North Haven YMCA and New Haven YMCA Youth Center on May 8, 2027; registration opens Feb 19 and first 100 pre-registrants receive a giveaway.
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 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
Multi-format event at Sacred Heart University featuring 90 minute stair climbs, a 90 minute walk challenge, and a five day virtual step challenge.