Middlefield
Trail Running Calendar near Middlefield 2026-2027
Explore the top trail runs near Middlefield 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.
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.
Trail races in Burlington CT offering 8K and 5K on mixed technical trails with notable local landmarks and a Burlington Land Trust fundraiser.
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.
An off road 50K from Guilford Lakes School through rocky forest roads and single track, with aid stations, time cutoffs, and staggered entry fees.
November 2026
A rolling loop trail 10K in Bloomfield CT on November 1 2026 with technical single track, a three hour cutoff, and proceeds partly to NAMI.
Trail races at YMCA Camp Sloper offering a 400-minute loop event and a 4-mile two-lap race on a roughly two-mile wooded course with one main aid station.
An accurately measured 8K cross-country race at the MDC Reservoir Complex in West Hartford with gravel, trails and fields and USATF sanction pending.
A community Thanksgiving trail event on 11/26/2026 at Mill Pond Way Trail with a 3.5 mile run or walk, chip timing, post race yoga for participants, free water and snacks, and proceeds benefiting endometriosis research.
December 2026
A repeated 3.3 mile out and back on the Tower Trail at Sleeping Giant State Park, with four hour and eight hour options and a cupless aid station at start and finish.
April 2027
May 2027
Camp Mountain Laurel offers a family color run plus a 5K trail run and 5K trail walk at Hamden/North Haven YMCA and New Haven YMCA Youth Center on May 8, 2027; registration opens Feb 19 and first 100 pre-registrants receive a giveaway.