Trail Running calendar near Ridgefield 2026-2027

Run a scenic quarter marathon at West Hartford Reservoir on April 11, 2026, as the Hartford Track Club hosts a small, timed field limited to 150 runners. Enjoy chip timing, post race treats and a friendly, looped trail course.

Join Last Chance's Run for the Rescue, a scenic 5K at Blydenburgh Park on April 11 with virtual entry through Apr 19. Bring leashed dogs, enjoy trails and refreshments, and support Last Chance Animal Rescue.

Run or walk the John Jay Community Trail Race in Cross River through scenic wooded trails and rolling hills, with 5k, 4k walk and a Kids Jay Dash on the track. A family friendly community event that finishes on the John Jay Contest Field.

Run a scenic all terrain 5K through Stamford Museum and Nature Center, looping Bendel Pond and passing farm animals. Bring kids for a fun run with Petunia the Scottish Highland cow and support the museum.

Shore2Shore in East Islip on April 18, 2026 offers 50K and 25K trail races along the Long Island Greenbelt Trail, finishing at Heckscher State Park. Enjoy scenic coastline, full aid stations, and a two hour volunteer or donation option.

Take on the Traprock 50 at Penwood State Park in Bloomfield, CT on April 18, 2026. Choose a rugged 50K of three rolling, rocky loops or a single 17K loop along technical single track and scenic forest roads. Bring your own cup.

Join the final Conquer The Trail Race on April 18 in Dobbs Ferry at Mercy University for a scenic 7.5k on the Croton Aqueduct Trail. Celebrate Mercy's 75th, snag a commemorative shirt, and support the Mav Market.

Join the Brooklyn Cider House Spiked Apple 5K in New Paltz on April 19, 2026 for a chip timed run or walk. Enjoy a tee, cider pour, donut and a finisher medal that doubles as a bottle opener for a festive post race celebration.

Squatchywaska Mountainfest in Ellenville NY on April 25, 2026 is a rugged trail test on the Shawangunk Ridge with a 25K and a 10 mile option over steep climbs and technical singletrack. Field capped at 150 and proceeds benefit Run Wild.

The Wawayanda Trail Fest will take place in Highland Lakes on Saturday 25 April 2026. You can run between 21 and 100 kilometers.

Women focused trail run at Lake Mohegan offering a runnable 5K loop, a 10K two lap option and a 4 hour loop challenge. Expect scenic trails, medals for finishers and post race snacks; nonbinary runners are welcome.

Celebrate the 52nd Jack Bristol Lake Waramaug Ultra on April 26 in Kent Connecticut with 100K, 50 Miler, and 50K options on scenic rolling loops around the lake. Fast paved roads, four aid stations, and a friendly finish at Lake Waramaug St..

Enjoy a spring 10k trail race in Cross River, NY on April 26, 2026, winding through scenic park trails. Entry is by lottery with registration opening January 2, 2026, perfect for trail runners seeking a well organized challenge.

Join the XC Summer Series, a friendly Tuesday night 5K in Parsippany with chip timing and after race refreshments. Open to all ages and abilities, walkers welcome and affordable single night or full series pricing.

Take on the VCP50k, a 50 km ultramarathon through Van Cortlandt Park in the Bronx on May 2, 2026, featuring the classic Tortoise and Hare looped course with roots, rocks and 2,200 feet of climbing. Finishers get a custom medal, limited edit..

Run to Remember on May 2, 2026 in Red Hook NY offers scenic 5K and 10K trail runs plus a 5K walk through meadows, orchards and forest. Honor loved ones and enjoy community spirit with cash prizes for top finishers.

Take on Breakneck Point Trail Runs in Beacon, NY on May 3, 2026, with half and full mountain courses over rugged, technical trails, steep climbs, and sweeping views. Expect big elevation, aid stations, informal camping, and a lively trail c..

Blue 2 Blue Challenge is a tough 50K on New Haven's blue blazed trails, featuring rocky technical terrain and big climbs linking West Rock and Quinnipiac. Entry is by vetted waitlist and the race enforces strict cutoffs so come prepared.

Take on scenic singletrack at the Mount Archer Trail Race in Lyme CT on May 3, 2026 with a tough 9.2 mile loop or a fun 3 mile sprint. Chip timed results, post race food and drinks, and proceeds support the Lyme Fire Department and Lyme Amb..

Enjoy a scenic 5 mile trail run at Muscoot Farm in Katonah/Somers on May 17, 2026. Family friendly kids races and Farm Bucks to spend at the Muscoot Farmer's Market add festival fun after the finish.