Stratford
Trail Running Calendar near Stratford 2026-2027
Explore the top trail runs near Stratford for 2026-2027! We've gathered 41 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
Timed trail running at Gurski Farm in Brookfield CT on a rolling four mile loop with 8 hour, 4 hour, and a new 5K canicross option.
A community 72nd anniversary event in Lake Ronkonkoma with a timed 5K run/walk and an untimed fun run on mixed pavement, grass and trail surfaces.
A 46th annual 4K cross country at the VA Golf Course in Northport with proceeds supporting hospitalized and homeless veterans; includes a free short fun run and a virtual 4K.
Timed laps at New Canaan High School Track where adults run for 14 minutes and 48 seconds and kids run one 400 m lap, with proceeds supporting the Ram Council Foundation.
A technical 10k trail race at Ward Pound Ridge Reservation with a parallel November Raven 100k Challenge offering badge-based achievements and a wooden finisher woodallion.
Trail event at Alice Newton Street Park in Woodbridge CT offering a 4 mile trail run and a 2 mile woodland walk, with shirts, refreshments and awards.
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.
An inaugural backyard ultra at Cranbury Park where runners repeat a 4.167 mile loop each hour until only one runner completes a lap.
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.
A memorial 5K run and walk on the cross country course in Danbury offering a chance for friends, family and teammates to gather and remember.
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.
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.
Charity 5K and timed 1 mile walk/run at Darien High School on November 27, 2026 supporting The Depot, with family activities and bib pickup options.
December 2026
Timed trail event at Sleeping Giant State Park with repeated 3.3 mile out and back laps on the Tower Trail and 4 hour or 8 hour options.
Third annual 5K Reindeer Run/Walk on the Joel Barlow cross-country course in Redding, CT with festive attire encouraged and proceeds to the Class of 2029.
An 8k trail race at Sunken Meadow Park with hills, boardwalk sections and a postrace holiday cookie fest; net proceeds benefit local charities.