Roxbury
Trail Running Calendar near Roxbury 2026-2027
Explore the top trail runs near Roxbury for 2026-2027! We've gathered 35 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
December 2026
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
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.
April 2027
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.
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.
A USATF sanctioned 10K trail race in Cross River, NY on April 25, 2027, with entry by lottery and a $58 fee that includes park entry.
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 and 1.5 mile walk at Millbrook Vineyards & Winery on May 15, 2027, featuring a mostly grass cross country course and a post run wine pour.
An elimination loop race on Ragged Mountain in Berlin CT where runners repeat a roughly 3.11 mile loop each hour until one remains; field limited to 55.
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 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.