Connecticut
Connecticut Trail Running Calendar 2026-2027
Explore the best trail runs in Connecticut for 2026-2027! Our updated list features 54 exciting trail runs across the region. Find your next trail run in Connecticut below and join the trail community at these great events!
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.
An obstacle-based 5K at Short Beach in Stratford that raises funds for the Sterling Community Center and includes 18 plus obstacles, shirts, medals and family participation rules.
A 56 mile group run along the Farmington Canal Heritage Trail from West Suffield to New Haven on September 12, 2026, fundraising for Mental Health Connecticut with mostly self support.
Trail running at Macedonia Brook State Park near Kent CT with 12K, 25K and 50K options on technical single-track trails and cupless aid stations.
A free 3 mile out-and-back beach run at Westerly Town Beach held at low tide. The community event is organized by the Westerly Track Club and the Stavros family as a memorial run.
A community trail event at Ives Farm featuring a 5K, an elementary school relay, a free Pumpkin Dash for young children, family activities, and free training sessions.
A community fundraiser in Pomfret Center with a trail 5K and a 0.5 mile kids run supporting the Pomfret Community School PTO. Early and later registration fees differ and awards plus finisher medals are given.
Trail races in Ridgefield CT offering a single loop of about 4.25 miles or a double loop of about 8 miles through Hemlock Hills and Pine Mountain. The technical, rocky course starts and ends at the Lake Windwing ballfields.
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.
Trail race in Cockaponsett State Forest offering 4 or 9 mile routes over roots, rocks and hills with water stations and proceeds to PanCAN.
Trail races in Burlington CT on September 26, 2026 offering 8K and 5K routes on varied single and double track through Tunxis Trail landmarks.
Trail races on the restored Moosup Valley State Park Trail in Sterling CT with 5K, 8K, 10K and a kids fun run plus postrace food and shirt or medallion options.
October 2026
A veteran-run series of elevation-based mountain endurance events at Mohawk Mountain CT and Amicalola Falls GA, offering seven solo and team formats from 12 to 84 hours.
A 30 hour loop ultrarun in Roosevelt Forest CT on 2.5 mile laps offering distances to 100 miles with a finisher buckle and a single pavilion aid station.
Trail races at Bradford Preserve on October 3, 2026 feature 5K, 10K and a free kids run on dirt trails with seasonal course markings and a required orange clothing rule per state regulations.
Trail event at Great Hollow Lake on October 3, 2026 featuring 5K and 12K races plus a kids fun run, with in-person and virtual options on a USATF sanctioned course.
Trail marathon in Ashford CT on October 4, 2026, offering a 26.4 mile trail race and a two-runner relay on the Nipmuck Trail.
A fall trail race day in Norfolk, CT offering 5K, 10K and a half marathon with steep climbs, private-trail sections, a cupless policy with water stations, and on-site food and beverage vendors.
A 5K trail run and an accessible short run/walk on private Gemstone Farm in Wilton, CT on 10/10/2026, with farm access, post-event food and entertainment, supporting The Prospector.
Trail races at Mohawk Mountain Ski Area on October 11, 2026 offering 5K, 10K, Half Marathon and Marathon over steep ski slopes and forest trails.