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Trail Running calendar near Pittsfield 2025-2026

We have found 25 Trailruns within 80 miles of Pittsfield. See below where and when you can find the races.

Amy's Adventure Race for the Lake

Bolton Landing - 45 mi from Pittsfield

Run Amy's Adventure Race for the Lake in Bolton Landing, NY through scenic Adirondack trails. Choose 4.5 or 10 mile courses or run virtually, enjoy lake views and a postrace beer while supporting the Lake George Land Conservancy.

Trapp Lodge Mountain Marathon

Stowe - 48 mi from Pittsfield

Take on the von Trapp Mountain Marathon at Trapp Family Lodge in Stowe Vermont with half and full options on a rugged 13.1 mile loop featuring steep climbs and a summit scramble to Round Top. Enjoy sweeping views of Mount Mansfield and a th..

Ghostly Gallop Trail 5K

Milton - 61 mi from Pittsfield

Join the Ghostly Gallop Trail 5K on Sunday October 25 in Milton Vermont for a spooky run along the Laura's Tears trail at Arrowhead Golf Course. Costume friendly with prizes, post race refreshments, and family fun.