Stratford
Trail Running Calendar near Stratford 2026-2027
Explore the top trail runs near Stratford for 2026-2027! We've gathered 35 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
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.
Trail races at Tarrywile Park in Danbury offering Marathon, Half Marathon and 10K on a loop course with technical single-track, substantial elevation gain, and cupless aid stations.
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.
A trail half marathon at Roosevelt Forest on November 21, 2026 featuring eight 1.64 mile loops, on-course aid, commemorative swag, and podium awards for top male and female finishers.
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.
3.5 mile trail run and walk around Scoville Reservoir with chip timing, post-race yoga, medals, swag and age-group awards.
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.
A trail only 8K at Sunken Meadow State Park in Kings Park, NY on December 6, 2026, with a post-race raffle and holiday cookie fest; proceeds support local charities.
A backyard ultra at Blydenburgh County Park: runners repeat a 4.167 mile loop each hour until one completes the final loop; proceeds support Long Island trail maintenance.
A 5 mile winter trail race at Mountain Lakes Park in North Salem NY with start and finish in the Yurt Village, a central firepit, and proceeds supporting park trail projects.
An 8 hour loop event at Lake Wintergreen in Hamden CT with 1.6 mile loops, one aid station, on course snacks and a 50 runner limit. Proceeds support Doctors Without Borders.
March 2027
Trail events at Sunken Meadow State Park on a roughly 1.4 mile loop with one hour and three hour formats awarding titles for greatest distance covered.
A 6 hour trail ultra at Roosevelt Forest in Stratford CT with a 2.3 mile loop, on-course food and hydration, a 50 person field, and podium awards for top men and women.
April 2027
A community trail event in Cross River, NY featuring a 5k trail race, a 4k walk on the same trails, and a 200 meter kids dash on the contest track.