Killingworth
Trail Running Calendar near Killingworth 2026-2027
Explore the top trail runs near Killingworth for 2026-2027! We've gathered 21 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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.
An off‑road 50k through southern Connecticut woodlands from Guilford Lakes School, featuring rocky single track and forest roads with a 10 hour cutoff.
A 5K Run / Walk and Kids Fun Run at Hallock State Park on October 25, 2026, with a virtual 5K option. Proceeds support the Long Island Greenway and include a post-race wine crawl with vendor specials for participants 21 and over.
November 2026
A fundraising 5K at Riverside Park supporting Riverfront Recapture's Community Rowing Program with running, rowing, and erg events.
Trail races at YMCA Camp Sloper in Southington CT with a 400 minute timed loop event and a four mile two lap race organized by CT Trailmixers.
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 at Southington High School on November 22, 2026, features wooded cross-country routes, a new track finish, and a Kid's Fun Run.
A Thanksgiving trail event at Scoville Reservoir with a 3.5 mile run or walk, chip timing, post-race yoga, swag, and proceeds supporting the Endometriosis Foundation of America.
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.
December 2026
Test your endurance at Sleeping Giant State Park by completing as many 3.3 mile loops as possible in 4 or 8 hours on the scenic Tower Trail.
An eight hour looped run at Lake Wintergreen in Hamden CT with 1.6 mile laps, one aid station, provided food and a 50 runner limit; proceeds benefit Doctors Without Borders.
March 2027
Chip timed 5k run and walk at Osprey’s Dominion Vineyards in Peconic, NY on March 20, 2027, over a two lap cross country loop with a postrace wine pour for eligible participants. Registration includes a T shirt, collapsible wine glass and finisher me..
April 2027
May 2027