Trail Running calendar near North Haven 2024-2025

The Frosty Forest 5K is a unique trail running event taking place in Roosevelt Forest, Stratford, CT. This festive race encourages participants to embrace the holiday spirit by dressing in costumes while enjoying the natural beauty of the trails. Runners, joggers, hikers, and walkers are all welcome..

Seth's Fat Ass 50K is an exciting running event taking place in Springfield, MA, at Forest Park. Participants can choose to complete one, two, or all ten loops of the 50K course, with a total time limit of seven hours to finish. The event promises a fun atmosphere and includes custom schwag for all ..

The Frosty Woods - A Winter Way Over Yonder Trail Adventure is part of the 2024 Way Over Yonder Trail Run Series, taking place in Ringwood State Park. This event features a scenic course primarily composed of singletrack trails, with options for a Half Marathon, 10K, and 5K, catering to runners of a..

The 7th Annual Taco Trials is a unique running event held in North Haven, CT, where participants eat tacos while completing a one-mile loop. Competitors must run ten loops, consuming at least one taco to qualify for a medal. The event is known for its humorous and lighthearted atmosphere, with a rep..

The West Rock Winter Fat Ass Extravaganza is an exciting running event held in Hamden, CT, featuring 1.6-mile loops around Lake Wintergreen for a duration of eight hours. Participants can enjoy a variety of refreshments, including pizza, soup, and snacks, while an aid station provides essential supp..

The Cross Island 20 Miler Trail Run is an annual event organized by the Long Island Trail Running Club, taking place on December 28, 2024, in Massapequa, NY. This unique trail run spans from Long Island's South Shore to the North Shore, attracting enthusiastic runners who enjoy the camaraderie of li..

The Dar Snowshoe Scramble is a fun and low-key running event that offers participants the option to snowshoe or trail run, depending on snow conditions. The course is approximately 3.8 miles, with potential variations between 5k and 10k. The event emphasizes enjoyment over competition, with no forma..

The Squatchy Onesiefest 5K is a unique winter trail running event taking place at the Ramapo Valley County Reservation in Mahwah, NJ. Participants are encouraged to wear their favorite onesies for a fun and memorable experience. The race features a "lollipop" course that runners will complete twice ..

The Spring on the Trails Endurance Runs is an exciting annual event held in Lagrangeville, NY, featuring timed races of 3, 6, and 12 hours on a scenic 5k trail loop with approximately 250 feet of elevation gain per lap. Participants aim to complete as many loops as possible within their chosen time ..

The Northern Nipmuck Trail Race is a 16-mile trail running event held in Union, Connecticut, taking place on March 29, 2025. Organized by the Shenipsit Striders, the race features a scenic course that traverses the Nipmuck Trail and the Yale-Myers Forest. Participants can expect a challenging terrai..

The Sleeping Giant Trail Runs is an exciting and challenging trail running event set in Hamden, Connecticut, featuring two race distances: a 25K and a 50K. The course showcases the diverse terrain of Sleeping Giant State Park, with over 30 miles of trails that include smooth carriage roads and techn..

Big Bear Squatch North is an exciting trail running event set to take place in Bear Mountain, NY, featuring a variety of distances ranging from 5K to 50K. The course has undergone several reroutes in previous years due to storm damage, particularly from July 2023, which has affected trail accessibil..

The Traprock 50 is a challenging trail running event held at Penwood State Park in Bloomfield, CT, featuring two race distances: a 50K and a 17K. The course consists of approximately 10.5-11 miles per loop, with the 50K requiring three loops and the 17K one loop. Runners will navigate a mix of techn..

Shore2Shore is an exciting running event taking place in East Islip, NY, featuring a scenic 50K and 25K race along the beautiful Suffolk County Long Island Greenbelt Trail. Participants will experience a point-to-point course that starts at Sunken Meadow and finishes at Heckscher State Park, with fu..

The Sterling Squatch Half Marathon is a thrilling trail running event set in the stunning Gunks region, featuring two challenging courses: a 10-mile and a 25K route. Participants will navigate through picturesque mountain singletracks, experiencing breathtaking views, including the iconic Verkeerder..

The Jack Bristol Lake Waramaug Ultra Races, taking place on April 27, 2025, marks the 51st anniversary of this historic event, known as the oldest ultra race in Connecticut and the first 100K in the United States. Participants can choose from three distances: 100K, 50 miles, and 50K, all set on scen..

Leatherman's Loop is a popular 10k trail race held annually in Cross River, NY, attracting participants of all ages, from 7 to 107. The event is scheduled for April 27, 2025, and features a lottery system for entry due to its high demand. The registration fee includes the park's entry fee, streamlin..

The Forgotten Forest Ultra Run, taking place in Stratford, CT, is a unique 9-hour trail running event set in the scenic Roosevelt Forest. Participants can choose to run, jog, hike, or walk on a well-marked loop trail featuring an elevation gain of approximately 131 feet per loop. This friendly compe..

The Bear Mountain Trail Challenge is an exciting running event held at Bear Mountain State Park, located just an hour from New York City. Participants can choose from three race distances: a 50K, a half marathon (21K), and a 10K. The course features a diverse range of terrain, including short climbs..

The Breakneck Point Trail Runs, organized by Red Newt Racing, is a challenging trail running event set to take place on May 4, 2025, in Beacon, NY. Participants can choose between a half marathon (13.1 miles) and a full marathon (26.4 miles), both featuring significant elevation gains and technical ..