Connecticut
Connecticut Trail Running Calendar 2026-2027
Explore the best trail runs in Connecticut for 2026-2027! Our updated list features 50 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.
A family friendly, obstacle filled beach 5k in Stratford that raises funds for Sterling Community Center while supporting individual and team fundraising.
A noncompetitive fundraising group run along the Farmington Canal Heritage Trail covering about 56 miles from West Suffield to New Haven with a 14-hour cut-off.
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 trail race, a team relay for elementary students, a free kids Pumpkin Dash, and family fall activities.
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.
Experience the technical terrain of Cockaponsett State Forest with 4 and 9 mile trail races. Navigate hills and rocky paths in Chester to support PanCAN and the Blue Blazed Trail Race series.
Trail races in Burlington CT offering 8K and 5K on mixed technical trails with notable local landmarks and a Burlington Land Trust fundraiser.
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 15-mile trail event at Mohawk Mountain Ski Area in Cornwall, CT with 7,140 feet of elevation and a 12-hour limit; participants may run, hike, walk, or compete in a relay, with registration listed as free for the stated window.
A 30 hours looped trail ultra in Roosevelt Forest CT with multiple distance options, a 2.5 mile loop, single pavilion aid station, pacer rules, and finisher buckles at 100 miles.
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.
A 26.4 mile trail marathon in Ashford CT on October 4, 2026 with a two person relay option and a course of rocks, roots, mud, and wood bridges.
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 fall trail event at private Gemstone Farm in Wilton CT with a timed 3.1 mile race, an accessible short run or walk, live music and farm access.
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.