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.
September 2026
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.
Experience a technical trail race through the Nassahegan State Forest and Devil’s Kitchen in Burlington, featuring 5K and 8K distances on the Blue-Blazed hiking trail system.
October 2026
A community fall event at Lake Wallace in Belchertown with a 5K, an accessible 1K, a Roll & Stroll, vendors, live music, and donations to the Lake Wallace Gift Account.
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.
A community 5K in Bolton, CT on 10/17/2026 along the Hop River rails to trails, with a $30 entry donated to Project Purple to support pancreatic cancer awareness.
A charity 5K on the scenic trails at Norbrook Farm Brewery in Colebrook CT supporting the Lymphoma Research Foundation with local beer available after the run.
November 2026
Run a technical 10k loop through the rocky single track trails of Penwood State Park in Connecticut to support mental health awareness.
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
A point to point trail challenge across Connecticut following the New England Trail from the Massachusetts border to the Long Island Sound.