Tackle the Trail (TM) 2026

Tackle the Trail is a point-to-point trail race in Northeast Connecticut, held on the third Saturday in October. Runners can choose a marathon, half marathon, 10K, or a marathon relay with up to five team members. The race uses the northern part of the Air Line Trail State Park, so even the shorter options are tied to the same rail-trail setting rather than a closed-road city loop. The route runs from Windham through downtown Putnam, with mixed terrain, bridges, and technical loops along the way. Parts of the course are quiet and wooded, while the town sections bring in spectators and local support. More than 100 volunteers help run the event, and local business partnerships make it part of the fall race calendar in Connecticut’s northeast corner. It is also a manageable trip for New England runners, about 45 minutes from Providence and about an hour from Boston.