Connecticut
Connecticut Trail Running Calendar 2026-2027
Explore the best trail runs in Connecticut for 2026-2027! Our updated list features 41 exciting trail runs across the region. Find your next trail run in Connecticut below and join the trail community at these great events!
October 2026
An off‑road 50k through southern Connecticut woodlands from Guilford Lakes School, featuring rocky single track and forest roads with a 10 hour cutoff.
A charity 5K on the scenic trails at Norbrook Farm Brewery in Colebrook CT supporting the Lymphoma Research Foundation with local beer available after the run.
A fall trail event at Grills Preserve in Westerly with 10 mile and 10 km courses across single-track trails and riverfront sections. Club timing is used, orange clothing is required, and post-race refreshments are provided.
November 2026
Timed trail running at Gurski Farm in Brookfield CT on a rolling four mile loop with 8 hour, 4 hour, and a new 5K canicross option.
A 10K trail loop in Bloomfield CT on November 1, 2026, on technical single track in Penwood State Park with a three hour cutoff and proceeds supporting NAMI.
A fundraising 5K at Riverside Park supporting Riverfront Recapture's Community Rowing Program with running, rowing, and erg events.
Timed laps at New Canaan High School Track where adults run for 14 minutes and 48 seconds and kids run one 400 m lap, with proceeds supporting the Ram Council Foundation.
A Thanksgiving themed chip timed 5k at Stonington Vineyards on November 8, 2026. The event features vineyard scenery and includes a t shirt, a portable wine glass, a finisher medal that doubles as a wine stopper and a wine pour.
A family friendly run and walk at West Thompson Dam on November 8, 2026 featuring a timed 5K trail run, a 3K untimed walk and a free kids 1/4 mile run; proceeds support local trails, parks and a food pantry.
A 100 percent cross country 5K at White Memorial Foundation & Conservation Center in Litchfield with natural trail footing, a midcourse hill, on-site outhouses, and Sawmill Field parking.
Trail event at Alice Newton Street Park in Woodbridge CT offering a 4 mile trail run and a 2 mile woodland walk, with shirts, refreshments and awards.
Inaugural backyard ultra at Cranbury Park in Norwalk on November 14 with repeated 4.167 mile loops, alternating loop direction every four hours.
Experience technical single track trails and significant elevation gain at Tarrywile Park with marathon, half marathon, and 10k race options in Danbury.
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.
Trail event at YMCA Camp Sloper offering a 400 minute timed loop race and a 4 mile two lap option on a flagged, roughly two mile trail course.
A memorial 5K run and walk on the cross country course in Danbury offering a chance for friends, family and teammates to gather and remember.
An accurately measured 8K cross-country race at the MDC Reservoir Complex in West Hartford with gravel, trails and fields and USATF sanction pending.
Inaugural Stride for the Knights 5K on November 22, 2026 at Southington High School features a wooded cross country course and a kids fun run.
Trail turkey trot in Brooksvale Park, Hamden CT on November 22 2026 offering 10K and 5K races, a food drive, and post-race bagels and donuts.
Second annual Thanksgiving 3.5 mile trail run and walk around Scoville Reservoir in Wolcott CT supporting endometriosis research with post-race yoga and finisher medals.