Westfield
Trail Running Calendar near Westfield 2026-2027
Explore the top trail runs near Westfield for 2026-2027! We've gathered 14 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
September 2026
Charity 5K run and 1.5 mile walk in Huntington MA on a mixed pavement, field and trail course that finishes at Littleville Dam.
A noncompetitive fundraising group run along the Farmington Canal Heritage Trail covering about 56 miles from West Suffield to New Haven with a 14-hour cut-off.
A 5K trail run at Winding Trails in Farmington on the designated course around Walton Pond, with registration from February 20 to September 20 and a $35 fee; overall and age-group awards plus a prize for the first local finishers.
Trail races in Burlington CT offering 8K and 5K on mixed technical trails with notable local landmarks and a Burlington Land Trust fundraiser.
October 2026
Join the annual Run Stanley event at Stanley Park for a variety of trail races including a 5K K9 run and an accessible 1 mile stroll. Support local wildlife sanctuary maintenance while enjoying a community day in the park.
A fall 5K and 2 mile walk at Ashley Reservoir in Holyoke supporting Legacy Equine Center & Sanctuary with scenic water views and local wildlife.
November 2026
A rolling loop trail 10K in Bloomfield CT on November 1 2026 with technical single track, a three hour cutoff, and proceeds partly to NAMI.
A 5K fundraiser at Riverside Park offering run, walk, erg and rowing options to support Riverfront Recapture's community rowing program.
An accurately measured 8K cross-country race at the MDC Reservoir Complex in West Hartford with gravel, trails and fields and USATF sanction pending.
April 2027
June 2027
Point to point trail running on the New England Trail with 112 mile and 50 mile options, requiring self support and crew assistance along a blue blazed unmarked route.