Simsbury
Trail Running Calendar near Simsbury 2026-2027
Explore the top trail runs near Simsbury for 2026-2027! We've gathered 20 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
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.
Trail races at Mohawk Mountain Ski Area in Cornwall, CT on October 11 with 5K, 10K, half and full marathon courses over ski slopes and Mohawk State Forest.
A 3.5 mile trail run and walk on the scenic, flat Mill Pond Trail at Woodtick Recreation in Wolcott CT on October 17, 2026. Tiered online registration is available and a post-event meal is included with registration.
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.
Trail 5K and a kids one mile fun race on a 33 acre campus in Middlefield CT with breakfast treats and finisher medals.
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
A 10 km rolling loop on technical single track in Penwood State Park, organized by CT Trailmixers, with no aid stations and proceeds partly to NAMI.
A fundraising 5K at Riverside Park supporting Riverfront Recapture's Community Rowing Program with running, rowing, and erg events.
A 100 percent cross country 5K at White Memorial Foundation & Conservation Center in Litchfield with natural trail footing, a midcourse hill, on-site outhouses, and Sawmill Field parking.
Trail races at YMCA Camp Sloper with a 400-minute loop challenge and a 4-mile option on a marked, varied-surface course with aid station support.
An accurately measured 8K cross-country race at the MDC Reservoir Complex in West Hartford with gravel, trails and fields and USATF sanction pending.
Inaugural Stride for the Knights 5K on November 22, 2026 at Southington High School features a wooded cross country course and a kids fun run.
3.5 mile trail run and walk at Mill Pond Way Trail in Wolcott, CT with post-race yoga, chip timing, medals, and proceeds benefiting endometriosis research.
Off-road 5 km and 5 mile run plus a 5 km ruck in South Glastonbury on November 28, with a kids fun run and a post-event chili, s'mores and brewery beverages.
April 2027
May 2027
An elimination loop race on Ragged Mountain in Berlin CT where runners repeat a roughly 3.11 mile loop each hour until one remains; field limited to 55.
June 2027
Point to point trail event in Connecticut with 112 mile and 50 mile options along the New England Trail and substantial vertical gain.