Bolton
Trail Running Calendar near Bolton 2026-2027
Explore the top trail runs near Bolton for 2026-2027! We've gathered 19 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
October 4, 2026 NipMuck Trail Marathon in Ashford CT offers a 26.4 mile trail with rocks, roots and mud, plus a two person relay option.
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 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 community fundraiser on October 25, 2026 featuring a timed 5K trail, a 1K pre-teen road race, a 5K walk, children's games and a costume contest.
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 multi terrain 5K, a scenic 2 mile walk and a kids loop at Old Sturbridge Village on November 15, 2026 with awards and participant shirts.
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.
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.
March 2027
Trail race on March 28, 2027 in Union CT covering about 16 miles on the Nipmuck Trail through Yale Myers Forest with parking at Bigelow Hollow State Park.
April 2027
Trail races at Deer Lake Outdoor Center in Killingworth CT with an approx 5 mile course, about 500 ft of elevation gain, and a timed 1 mile kids run.
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.