Trail Running calendar near Pawling 2024-2025

The Roxbury Thanksgiving Day Charity Race is a 5K running event held annually in Roxbury, Connecticut, aimed at promoting community spirit and supporting local charities. Participants run a 3.1-mile course at the Everett B. Hurlburt Community Park.The event encourages runners of all ages and abiliti..

The Squatchy Leftovers Trail Race is set to take place at South Mountain Reservation in West Orange, NJ, offering participants the choice of running or hiking distances of 5K, 10K, 25K, or 50K. This family-friendly event supports the non-profit organization Bigger Than The Trail, which provides cost..

The PPTC Endurance Fest is an exciting running event held in Prospect Park, Brooklyn, featuring a 50-mile and a 50-kilometer race. Participants will navigate a looped course that honors NYC's road ultra heritage, completing either 9 or 15 loops of 3.33 miles each. The race starts and ends near the L..

Rob's Trail Run Edition is a running event taking place at Stillwell Woods Preserve in Woodbury, NY, on December 1, 2024. The event features two main races: a 5K Adult Trail Run and a 5K High School or Youth Trail Run, catering to participants of different age groups. This event aims to honor the me..

Gorge après Gorge is an annual 5k trail run and free family fun walk held in the Hilltowns, featuring a scenic course along the Wild and Scenic Westfield River. Participants receive cookie medals, and unique knitted hats are awarded to top finishers. The event includes a community potluck with baked..

The Tower Tag Challenge is an exciting running event taking place at Sleeping Giant State Park in Hamden, CT. Participants can choose between 8-hour and 4-hour options, racing up and down the scenic Tower Trail, which leads to an Observation Tower. Each loop covers approximately 3.4 miles, allowing ..

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, NJ. This event features a scenic winter trail running experience with courses for a Half Marathon, 10K, and 5K, each offering unique challenges and beautiful vi..

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 to provide custom schwag for all participants, inclu..

The Frosty Forest 5K is a unique running event taking place in Roosevelt Forest, Stratford, CT. This will be the final edition of the race, inviting participants to enjoy a scenic trail run while embracing the holiday spirit. Runners can choose to run, jog, hike, or walk the 5K course, with the opti..

The Squatchy Solstice 5K, hosted by Sassquad Trail Running and the New York-New Jersey Trail Conference, takes place at Hilltop Reservation in Cedar Grove, NJ. This unique trail run celebrates the shortest day of the year, with proceeds supporting trail maintenance efforts. Participants can expect a..

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 an aid station with various refreshments, including pizza, soup, and snacks. The event encourages self-sup..

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 and hiking event held in West Orange, NJ, designed for participants of all ages and skill levels. Scheduled for January 25, 2025, this event features various distances, including a 5K, 3-hour, and 6-hour challenge, all set within the scenic South Mounta..

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 course features a scenic "lollipop" loop that is beginner-friendly,..

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 ages and abilities. The event supp..

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

The Northern Nipmuck Trail Race is a 16-mile trail running event held at Bigelow Hollow State Park in Union, CT. Revived in 2022 after being discontinued in 2012, the race maintains a low-key atmosphere and a friendly community spirit. The course follows the Nipmuck Trail, featuring technical terrai..

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..