Trail Running calendar near Pawling 2024-2025

The West Rock Winter Fat Ass Extravaganza is an exciting running event taking place 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, grilled cheese, and snacks, while an aid station..

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 the South Shore to the North Shore of Long Island, attracting enthusiastic runners who enjoy the camaraderie ..

The NJ Trail Series SOMO Winter 3 is a running event taking place in South Orange, NJ, featuring three race distances: 5K, 10K, and 13.1 miles. The course is designed to incorporate a variety of terrains, including fire roads, single track trails, and hills, providing a challenging experience for pa..

The Frosty Fat Sass is an annual trail running event taking place in West Orange, NJ, designed for runners and hikers of all ages and abilities. Participants can choose from a 5K, 3-hour, or 6-hour race, all set in the scenic South Mountain Reservation. This event not only promotes outdoor activity ..

The YETI OR NOT Snowshoe Invasion is an exciting winter sports event taking place at Mountain Creek in Vernon, NJ. Participants can choose between a challenging 5k tromp across the mountain or a more relaxed Last Mile Fun Option. This event welcomes runners, walkers, and newcomers to snowshoeing ali..

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 scheduled for February 8, 2025, at the Ramapo Valley County Reservation in Mahwah, NJ. Participants are encouraged to wear their favorite onesies for a fun and memorable experience. The event features a scenic "lollipop" course that r..

The Mahlon Winter Donut Run features a scenic trail running event held at Saffin's Pond in Lake Hopatcong, NJ. Scheduled for February 9, 2025, participants can choose from three distances: a 5-mile course, a 10-mile course, and a half marathon (13.1 miles). The courses offer beautiful wooded trails,..

The Febapple Frozen 50M, 50K, 20M, and 10M is a running event taking place in South Orange, NJ, on February 22, 2025. Participants can choose from four distances: 50 miles, 50 kilometers, 20 miles, and 10 miles, all set within the scenic South Mountain Reservation. The race features a 10-mile loop c..

Squatchapple is a trail race event taking place on March 8, 2025, at the South Mountain Reservation in West Orange, NJ. Participants can choose from various distances, including 11 miles, 20 miles, 50K, and 50 miles, making it suitable for runners and hikers of all ages and abilities. The event supp..

The Livingston Oval Ultra is an annual running event held in Livingston, NJ, featuring three race durations: six hours, three hours, and one hour. Participants aim to complete as many laps around a certified flat and fast oval course as possible within their chosen time limit. The event promotes a s..

The Lenape Trail Run is a self-supported 34-mile running event taking place on March 8, 2025, in Millburn, NJ. Participants will gather at the Locust Grove trailhead and take a train to Newark, from where they will run back along the historic Lenape Trail. This trail, established in 1982, is one of ..

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 MCW Lenape Runventure is a unique running event taking place over two days, featuring the 36-mile Lenape Trail in Millburn, NJ. Participants can join on either March 29 or March 30, 2025, with a mandatory fundraising goal of $1,000 to support clean water initiatives in Uganda. The event offers a..

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 Morris County Empanada Trail Run is a vibrant running event taking place in Morris Plains, NJ, featuring both a 5K and a 10K run/walk. Participants can enjoy a scenic course that includes mixed terrain, such as dirt, grass, and gravel. Each registration includes a long-sleeved shirt, a unique fi..

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, and the organizers are currently assessing the trails for the 20..

The Spring SOMO Timed Trail Races is a running event scheduled for April 12, 2025, at South Mountain Reservation in South Orange, NJ. Participants can choose from various race formats, including a 3K loop, a 6K loop, and timed events lasting 1, 3, or 6 hours. The course features a mix of single trac..

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..