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Trail Running calendar near Windham 2026-2027

We have found 26 Trailruns within 80 miles of Windham. See below where and when you can find the races.

Megunticook Trail Festival

Camden - 73 mi from Windham

Run coastal ridgelines at the Megunticook Trail Festival in Camden Hills State Park on Sept 12, 2026. Choose 50K, 20k or 10k over rocky singletrack and ocean ledges. Entries are limited and Indigenous runners run free.

Mt. A Trail Challenge

York Harbor - 45 mi from Windham

The Mt. A Trail Challenge will take place in York Harbor on Saturday 19 September 2026. You can run 5 kilometers.

November 2026

TARC Stone Cat Trail Festival

Ipswich - 78 mi from Windham

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TARC Stone Cat Trail Festival at Willowdale State Forest in Ipswich, MA offers distances from a cider donut mile and youth run to serious ultras up to 100K. Rugged 12.5 mile loops of roots, rocks and rolling terrain make for a scenic, chall..