Norwalk
Trail Running Calendar near Norwalk 2026-2027
Explore the top trail runs near Norwalk 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
An inaugural backyard ultra at Cranbury Park where runners repeat a 4.167 mile loop each hour until one runner remains, with crew access and central aid near the corral.
Trail race at Tarrywile Park offering Marathon, Half Marathon and 10K on a loop course with roughly 3K of elevation and technical single-track.
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.
8th Annual Thanksgiving Turkey Trot in Somers NY with a 5K trail race and a 1 mile fun run, shirts, medals, age group awards, and packet pickup.
A trail 5K run and virtual option at Bethpage State Park on November 28, 2026, with a free Kiddie Dash, post-race refreshments, and donations benefiting the Never Stop Running Foundation.
December 2026
A weekend trail event in Blydenburgh County Park featuring a Backyard Ultra with 4.167 mile hourly loops and a separate 4.16 mile lapping race. A portion of proceeds supports the Long Island Greenbelt Trail Conference.
Experience an exclusive trail run through the scenic Roosevelt Forest in Stratford. This 5K event features a natural off-road course limited to a small group of participants and includes custom finisher medallions.
March 2027
A six hour trail ultra at Roosevelt Forest in Stratford CT on a 2.3 mile loop with roots, rocks and rolling hills; field limited to 50 participants.
A 5K trail run at Bethpage State Park with a free kiddie fun run, on-site refreshments, beer for ages 21 and up, and a virtual participation option.
April 2027
A 5K trail run/walk at Bethpage State Park with a kids run, virtual option, on-site amenities, and online age group recognition.
A community trail event in Cross River, NY featuring a hilly wooded 5K, a 4K walk through the main trail, and a 200 m kids dash on the contest track. Registration opens 8/24/2026 with limited pre-registration t-shirt incentives.
A 5K trail run/walk at Blydenburgh County Park in Smithtown, NY, on mixed-surface trails with on-site amenities and proceeds supporting Last Chance Animal Rescue.
Point-to-point 50K and 25K along the Suffolk County Greenbelt Trail from Sunken Meadow to Heckscher State Park, returning April 17, 2027.
A 10K spring trail race in Cross River NY on April 25, 2027; entry is by lottery and the $58 registration fee covers park entry.
May 2027
A nine hour timed trail ultra on a 2.2 mile loop through Roosevelt Forest in Stratford, CT. Entry is limited to 50 participants and awards go to the runners with the most miles by the race end.
A 5K run/walk at Bethpage State Park featuring soft trail sections, live results, free finish line photos, and awards for top overall male and female finishers.
A 5K trail run/walk at Blydenburgh County Park with on-site refreshments, a free kiddie dash, virtual participation, and donations benefiting the Never Stop Running Foundation.
A 5 mile trail race at Muscoot Farm on May 23, 2027 with two kids races on farm trails. The event is organized by Run the Farm Races and is sanctioned by USA Track and Field.
June 2027