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Trail Running calendar near Charlestown 2026-2027

We have found 103 Trailruns within 80 miles of Charlestown. See below where and when you can find the races.

Tarctic Frozen Yeti

Westwood - 61 mi from Charlestown

Experience a winter trail challenge at Hale Education featuring 15 mile and 30 hour options. Navigate three unique loops through the Massachusetts woods while testing your endurance and self reliance in cold weather conditions.

April 2027

Run Across CT

Thompson - 43 mi from Charlestown

A 123 mile point to point ultramarathon across Connecticut featuring about 57 miles of trail, a 36 hour cutoff, solo and relay options, and belt buckles for 200K finishers.

Sleeping Giant Trail Runs

Hamden - 65 mi from Charlestown

Trail races at Sleeping Giant Park in Hamden, CT offering a 25K loop with 3K+ vertical and a 50K two loop option. The course features technical singletrack, steep rock scrambles, aid stations, and finisher medals.

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