Chester
Trail Running Calendar near Chester 2026-2027
Explore the top trail runs near Chester for 2026-2027! We've gathered 11 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
Experience a community trail run through Elm Ridge Park benefiting the Rocky Hill Fire Department and Library. This event features a two loop trail course for adults and a fun medal race for kids.
September 2026
Experience a scenic 3.3 mile trail run or hike through the Oswegatchie Hills Nature Preserve. Support local land conservation while enjoying a timed course around Clark Pond followed by an awards ceremony with refreshments.
A 5K trail run at Winding Trails in Farmington on the designated course around Walton Pond, with registration from February 20 to September 20 and a $35 fee; overall and age-group awards plus a prize for the first local finishers.
October 2026
An off‑road 50K around Guilford, CT on rocky single track and rolling forest roads, with aid station cutoffs and recommended marathon-level experience.
A community run at Ives Farm hosted by Cheshire Community YMCA and Cheshire Land Trust. Features a trail 5K, a youth Y Cup relay with elementary teams, a free Pumpkin Dash for young children and family fall activities.
November 2026
Trail races at YMCA Camp Sloper on November 21, 2026 offering a 400 minute loop event and a 4 mile race with chip timing and on-course aid.
December 2026
A repeated 3.3 mile out and back on the Tower Trail at Sleeping Giant State Park, with four hour and eight hour options and a cupless aid station at start and finish.
April 2027
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.