Stratford
Trail Running Calendar near Stratford 2026-2027
Explore the top trail runs near Stratford for 2026-2027! We've gathered 40 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Four-day trail event in Rocky Point, NY featuring a 10.48-mile Pine Barrens loop with eight distance options from 10 miles to 150 miles.
A timed trail 5K at a private 150-acre farm in Wilton CT with an accessible short run, live music, food, and proceeds supporting The Prospector.
A scenic trail 5K at Blydenburgh County Park on October 11, 2026 with in-person and virtual options, race tee, refreshments, and age-group recognition.
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 through southern Connecticut woodlands from Guilford Lakes School, featuring rocky single track and forest roads with a 10 hour cutoff.
Trail running at Muscoot Farm with a 5 mile race and two kids races on October 25, 2026 in Katonah, NY.
November 2026
Experience a community-focused trail race featuring a 4 mile loop of rolling farm trails and single track with timed options, a 4 mile distance, and a 5K Canicross.
Community 5K and untimed fun run on November 7, 2026 at Sachem North High School in Lake Ronkonkoma NY, offering shirts, live results, photos, and age group awards.
A 4K grass cross country event at the Northport VA Golf Course with military and youth categories, a short fun run, awards, and proceeds supporting local veterans.
A trail 10k at Ward Pound Ridge Reservation on November 8, 2026 plus a monthlong November Raven 100k Challenge with a wooden finisher medallion.
A trail event in Manorville Hills with 3, 6, 12 and 24 hour options on a runnable 5K loop featuring about 270 feet gain per loop.
Inaugural backyard ultra at Cranbury Park in Norwalk on November 14 with repeated 4.167 mile loops, alternating loop direction every four hours.
A farm-based memorial 5K and kids fun run on 11/14/2026 at the Suffolk County Farm and Education Center raising funds for pancreatic cancer research.
Experience technical single track trails and significant elevation gain at Tarrywile Park with marathon, half marathon, and 10k race options in Danbury.
Trail half marathon and 5 mile at Brookhaven State Park on Nov 15, 2026, on single track and fire trails with awards, cash prizes, and finisher medals.
Experience a magical 13.1 mile trail race through the rolling hills of Roosevelt Forest. Complete eight loops of a wooded course while supporting a children's book drive in this unique costume friendly event.
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.
A ninth annual charity 5K in Roxbury, Connecticut on November 26, 2026, with a 3.1 mile out-and-back course near Everett B. Hurlburt Community Park. Proceeds support local ambulance and scholarship funds and a food pantry collection.
Post-Thanksgiving community races at Darien High School featuring a 5K and a 1 Mile walk/run with proceeds benefiting The Depot youth center.