Trail Running calendar near Woodbridge 2026-2027

Run or walk through 50 acres of beautiful vineyards in Peconic for a chip timed 5K event. Participants receive a finisher medal that doubles as a wine stopper and a celebratory pour of wine at the finish line.

A classic 16-mile trail run on Connecticut's Nipmuck Trail, known for its technical terrain and old-school vibe. Organized by the Shenipsit Striders, the event supports local trail stewardship. Registration is capped and no race day signups..

Course and Distances The Sleeping Giant Trail Runs take place at Sleeping Giant State Park in Hamden, Connecticut. The event offers two distances: 25 km: A single loop with over 3,000 feet of vertical gain. 50 km: Two loops of the 25 km co..

The Fool's Adventure is a ten hour foot rogaine on March 29, 2026 in Wayne, New Jersey. Competitors navigate more than 100 checkpoints across eight square miles of rugged wilderness using maps and a compass while recording checkpoint eviden..

Experience a technical 10 km trail race through the rugged terrain of Van Cortlandt Park in the Bronx. This annual event supports local trail maintenance and features unique local prizes for top finishers.

Run the perimeter of Heckscher State Park on smooth trails. Choose a 7-mile or 14-mile loop for a cupless, manually timed race. All finishers get a wooden medallion and a bucket hat.

Experience a scenic trail run through Bethpage State Park with the 4 Leaf Clover 5K. Enjoy a mostly flat course, post race refreshments, and a festive atmosphere supporting the Never Stop Running Foundation.

Tackle the rugged trails of Harriman State Park in this mountain trail run. Choose between a challenging 10K with 1,400 feet of climb or a half marathon with over 2,600 feet. The event supports local trail maintenance and includes a rucking..

Experience a clockwise loop race at South Mountain Reservation featuring timed options from one to six hours. This event offers a 1.88 mile course consisting of single track paths and fire roads for all distance preferences.

Course and Distance The Run Across CT 123 is a point-to-point ultramarathon that travels coast-to-coast across Connecticut, covering approximately 123 miles (200K). The route passes through 25 towns, starting in East Thompson and finishing..

Experience the 7th Annual Bunny Trail 5K at Bethpage State Park. Run or walk through scenic soft trails and grassy polo fields with options for an in person race, a virtual challenge, and a free kids run.

The Bimbler's Bash is a popular annual 10K trail run through the technical, rocky paths of Guilford's Westwoods. This entirely off-road event supports local land conservation and is known as a major single-distance race in Connecticut.

Run a unique quarter marathon distance on the paved trails of West Hartford Reservoir. This chip timed 6.55 mile race features a two loop course with post race treats and age group awards.

Join this dog friendly 5K trail run at Blydenburgh County Park to support animal rescue. Enjoy a scenic multi surface course with refreshments and professional timing included for all participants.

Experience a community trail event in Cross River featuring a competitive 5k race, a scenic 4k walk, and a 200m kids dash. Explore the wooded hills of the John Jay Community Trail ending at the campus contest field.

Run through a scenic nature center featuring farm animals and wooded trails. This all terrain event in Stamford offers a unique 5K course and a fun run for children ages five and up.

Experience a beautiful trail run through the Irvington Woods with 5K and 1K distances. This rain or shine community event features finishers medals for all participants and supports the Irvington Bulldog Booster Club.

The 11th Annual F.O.R 5k Trail Race takes runners through the scenic McDonald Nature Preserve in Wilbraham. This family-friendly trail run supports the local parks' maintenance fund.

The Shore2Shore is a scenic point-to-point trail run on Long Island's Greenbelt Trail, from the north to south shore. Choose between the 50K or 25K distance on this well-marked course. Registration includes a trail work volunteer requiremen..

The Traprock 50 features a rugged 50K and a 17K trail race on the rocky, rolling loops of Penwood State Park. It's a cupless event with chip timing, organized by volunteers to benefit local conservation groups. Runners should be prepared fo..