Simsbury
Trail Running Calendar near Simsbury 2026-2027
Explore the top trail runs near Simsbury for 2026-2027! We've gathered 15 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
November 2026
A 10K trail loop in Bloomfield CT on November 1, 2026, on technical single track in Penwood State Park with a three hour cutoff and proceeds supporting 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 event at YMCA Camp Sloper offering a 400 minute timed loop race and a 4 mile two lap option on a flagged, roughly two mile trail course.
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.
Second annual Thanksgiving 3.5 mile trail run and walk around Scoville Reservoir in Wolcott CT supporting endometriosis research with post-race yoga and finisher medals.
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
A 6.55 mile race at West Hartford Reservoir on April 10, 2027, run as two 3.275 mile paved loops with chip timing and a 150 runner limit.
May 2027
A Last Person Standing trail race on Ragged Mountain in Berlin, CT using repeat one-hour 3.11-mile loops until one runner remains; field limited to 55.
June 2027
Multi-day elevation events at Mohawk Mountain offering 12 to 84 hour Solo and team formats, on‑mountain tenting, ski patrol support, and timed lap formats to earn vertical gain.
Point-to-point trail event on the New England Trail offering 112-mile and 50-mile routes to Guilford, CT, with self-supported crews and route navigation required.
October 2027
Trail endurance events at Mohawk Mountain Ski Area offering solo and FlexRelay team options across 12, 24, 48, 72 and up to 84 hours with distances from 15 to 152.5 miles.