Connecticut
Connecticut Trail Running Calendar 2026-2027
Explore the best trail runs in Connecticut for 2026-2027! Our updated list features 55 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
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.
Run 56 miles across the entire state of Connecticut on a flat, scenic trail to raise funds and awareness for mental health initiatives.
Experience technical single track and sweeping views of the Catskill Mountains at this multi-distance trail race held in the scenic Macedonia Brook State Park.
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.
Experience a technical trail race through the Nassahegan State Forest and Devil’s Kitchen in Burlington, featuring 5K and 8K distances on the Blue-Blazed hiking trail system.
Trail races on the Moosup Valley State Park Trail with 5 km, 8 km, 10 km and a kids run plus post race food, awards and local charity support.
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 race at Great Hollow Lake on October 3, 2026 with timed 5K and 12K races plus a Kids Fun Run and virtual options benefiting a local scholarship and foundation.
Experience the NipMuck Trail Marathon in Ashford, a 26.4 mile course featuring technical terrain and a relay option through the scenic woods of Connecticut.
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.
Experience a trail run through Mohawk Mountain Ski Area and Mohawk State Forest featuring steep climbs and scenic fall foliage across distances from 5 km to a full marathon.
Experience a point to point trail race in Northeast Connecticut on the Airline Trail. Choose between marathon, half marathon, and 10K distances with individual or relay team options to support local student education.