Trail Running calendar near Pawling 2025-2026

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 Dar Snowshoe Scramble is a casual running event that embraces both snowshoeing and trail running, depending on snow conditions. Participants can expect a fun atmosphere with no frills, as there are no prizes or t-shirts. The course will range between 5k and 10k, and there will be loaner snowshoe..

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 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 course features a scenic "lollipop" loop that ru..

The Mahlon Winter Donut Trail Run & Hike features a scenic adventure through the beautiful trails of 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 event begins with packet pic..

The Febapple Frozen 50M, 50K, 20M, and 10M is a running event scheduled for February 22, 2025, in South Orange, New Jersey. 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 ..

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 skill levels. The event supports t..

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 challenging 34-mile running event taking place on March 8, 2025, in Millburn, NJ. Participants will meet at the Locust Grove trailhead and take a train to Newark, from where they will run back along the historic Lenape Trail. This self-supported run requires participants to..

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, organized by the Shenipsit Striders. Revived in 2022 after a hiatus, the race maintains a friendly, low-key atmosphere, attracting runners of all levels. The course traverses the Nipmuck Trail, featuring tec..

The Enchanted Forest Ultra Run is a unique 6-hour trail race set to take place on March 29, 2025, in Stratford, CT. This event features a 2.3-mile loop course with an elevation gain of 191 feet, perfect for both novice and experienced runners. Participants can run, jog, hike, or walk as many laps as..

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 Lost Brook Trail Race is an exciting running event taking place in Tenafly, NJ, featuring both 10K and 5K courses through the scenic Lost Brook Preserve. Participants will navigate a natural terrain filled with rocks, roots, and footbridges, making for a challenging yet enjoyable experience. The..

The Sleeping Giant Trail Runs is a challenging new race set in one of Connecticut's most iconic parks, known for its diverse trails. Participants can choose between a 25K and a 50K course, both featuring over 3,000 feet of elevation gain. The event showcases a mix of smooth carriage roads and techni..

The Big Bear Squatch North is a challenging trail running event taking place at Harriman State Park in Bear Mountain, New York. Scheduled for April 5, 2025, this event features a half marathon and a 10K race, both known for their rugged terrain, steep climbs, and breathtaking views. Participants can..

The Farm & Forest All-Terrain 5K & Kid Fun Run is scheduled for April 6, 2025, at the Stamford Museum & Nature Center in Stamford, CT. This exciting event features a scenic 5K course that begins at the Fedele Family Plaza and winds through Heckscher Farm, allowing participants to encounter various f..

The John Jay Community Trail Race is a competitive running event taking place in Cross River, NY, featuring a 5k race, a 4k Jay Walk, and a Kids Jay Dash. The 5k race is set on the challenging John Jay Community Cross Country Trail, which includes wooded areas and hilly terrain. The 4k Jay Walk offe..

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, 6K loop, and timed events lasting 1, 3, or 6 hours. The course features a mix of single track,..