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Trail Running calendar near Chesterfield 2025-2026

We have found 45 Trailruns within 80 miles of Chesterfield. See below where and when you can find the races.

Keene Family YMCA Fall Foliage Trail Race

Roxbury - 13 mi from Chesterfield

Hit the trails at the Keene Family YMCA Fall Foliage Trail Races in Keene, NH on Sunday, October 4, 2026, with 5K and 10K options through scenic fall woods. Enjoy chip timing, shirts for early registrants, and support local YMCA programs.

Midstate Massive Ultra Trail

New Ipswich - 31 mi from Chesterfield

Tackle the Midstate Massive Ultra Trail, a UTMB Index point to point across New England following the historic Midstate Trail. Choose 100 mile, 50 mile or 50k routes through mountains, fields, roads and rivers for a multi state adventure.

Wayland / HFC Striders XC Festival

Wayland - 66 mi from Chesterfield

Celebrate the 20th Wayland HFC Striders Cross Country Festival on October 11, 2026, a family friendly meet supporting Wayland High School programs. Youth 3K plus open 5K races, trophies and local sponsors make for a fun community day.