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Trail Running calendar near Winchester 2025-2026

We have found 42 Trailruns within 80 miles of Winchester. See below where and when you can find the races.

TARC Fall Classic

Carlisle - 11 mi from Winchester

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Trail Animals Running Club Fall Classic at Great Brook Farm State Park offers scenic trails and distances from 10K to 50 mile, plus a youth fun run and Mischief Mile. Aid stations and vegan options support runners in this cupless event.

Moosup Valley 10K All Trail Race

Moosup - 64 mi from Winchester

Hit the newly restored Moosup Valley State Park Trail on Sunday, September 27 for scenic 5K, 10K and a kids fun run on all trail terrain. Post race food and gear, leashed dogs welcome, and proceeds support the Rotary Club of Plainfield.