Trail Running calendar near Monroe 2025-2026

The New Paltz Pizza Challenge is a fun and unique 3.3-mile running event held in New Paltz, NY, starting at Water Street Market. The course is approximately 5 kilometers and offers participants a lively atmosphere with plenty of pizza to enjoy along the way. The event features prizes for the winners..

The Dirty Dozen 50K is a challenging ultramarathon held in Forest Park, Queens, New York City. The race features a 2.5-mile loop along the scenic Orange Trail, completed 12 times for a total of 50 kilometers. Each loop includes 300 feet of elevation gain, making the course deceptively tough with rol..

The Jug End Loop Ultra is a 6-hour ultra running event held at Jug End State Reservation in Egremont, Massachusetts. Participants run multiple laps of a scenic 4.2-mile course featuring woods, fields, and an apple orchard, with a challenging elevation change of 830 feet per lap. The course includes..

Raptor Ridge, presented by Peace, Love, Trails (formerly the Sanctuary 6.5), is a 6.5-mile trail race held at Westmoreland Sanctuary in Westchester County, New York. The route weaves through the sanctuary’s rugged, scenic trails across 669 acres and 8.5 miles of hiking trails. Start and finish are a..

The Barn-B-Q Trail Festival, held in Berkeley Heights, NJ, is a unique outdoor event combining trail running, hiking, and a lively barn party. Set in the historic Deserted Village of Feltville within Watchung Reservation, participants can enjoy self-guided trail tours ranging from 2 to 6 miles, with..

The FallApple is a trail running event held in South Orange, New Jersey, at South Mountain Reservation. Scheduled for early September, the race offers a variety of distances including 5K, 10K, half marathon, marathon, 50K, and 50-mile options. The course features a mix of fire roads, single-track tr..

The Cross-Connecticut Run for Mental Health Awareness is a unique 56-mile group running event held annually in Connecticut, following the scenic and flat Farmington Canal Heritage Trail from West Suffield to New Haven. This non-competitive challenge supports Mental Health Connecticut through fundrai..

The Wicked Mudder will take place in Southwick on Sunday 7 September 2025. You can run between 5 and 5 kilometers.

Macedonia Trail Race, staged at Macedonia Brook State Park in Kent, CT, offers 12K, 25K, and 50K distances through unparalleled single-track and lush forest trails. The course features grinding climbs, technical descents, and several viewpoints, including Cobble Mountain with an overlook where, on c..

The Storybook Half Marathon is a scenic 13.1-mile trail race held in Roosevelt Forest, Stratford, Connecticut. The course consists of eight loops on a 1.64-mile wooded trail featuring singletrack and doubletrack paths with roots, rocks, and gentle hills, offering a charming yet moderately challengin..

Run for the Hills is the 4th Annual 5K trail run/walk held at the Oswegatchie Hills Nature Preserve in Niantic, CT. The route winds along hiking trails around the preserve’s perimeter, including a scenic stretch by Clark Pond, with exposed rocks and roots to challenge runners and walkers alike. Proc..

Located at Lakeside Park in Pawling, New York, the Pawling 24 Hour Trail Running Festival is the sixth edition of the endurance event, offering 24-, 12-, 6-, and 3-hour races (including a 12-hour night start). Runners tackle a 1.68-mile loop made up of pavement, grass, and single-track, with about 1..

The Wahaneeta Trail Run is a 5K trail race held in Westerly, Rhode Island, located on Moorhouse Road. Scheduled for September 13, 2025, it is the first event in the WTAC Fall Trail Race Series, which includes four races with a discount for registering in multiple events. This race embraces an "old s..

The PCS Harvest Hustle 5K & Kids Run is a community-focused event held at Pomfret Rec Park in Pomfret Center, Connecticut. It features a 5K trail run and a kids' fun run of half a mile, supporting the Pomfret Community School Parent Teacher Organization. The PTO uses funds raised to enhance educatio..

The Shawangunk Ridge Trail Run (SRT) is a challenging trail running event held in Rosendale, New York, featuring three race distances: a 70-mile ultra, a 30-mile race, and a half marathon. The course follows the scenic 70-mile Shawangunk Ridge Trail, which stretches from High Point State Park in New..

The Where the Pavement Ends Single & Double Loop is a trail running event held in Ridgefield, Connecticut, starting and finishing at the Lake Windwing ballfields. Scheduled for September 14, 2025, the race offers two options: a 4.25-mile single loop and an approximate 8-mile double loop through the..

The Charlie Stavros Memorial Beach Run is a free, 3-mile race held at Westerly Town Beach in Westerly, Rhode Island. Organized by the Westerly Track Club and the Stavros family, this event takes place at low tide, featuring a scenic out-and-back course of 1.5 miles each way along the beach. The run..

The Wild Goose Trail Festival takes place at Wawayanda State Park in Hewitt, New Jersey, offering a variety of trail running events over September 20-21, 2025. Distances range from a 1-mile kids run to a challenging 100-mile ultramarathon with a generous 36-hour cutoff, making it ideal for first-tim..

The Angevine Farm Trail Festival, held annually in Warren, Connecticut, offers a scenic and challenging trail running experience through grassy fields, land trust trails, state forest paths, single track, and dirt roads. The event features multiple distances including a half marathon, a new 8-hour r..

The Gardiner Dump Run is a scenic trail running event held in Gardiner, New York, featuring a 5k race with an option to complete two laps for a 10k distance. The course winds through single-track trails along wooded hillsides near the Wallkill River and untamed fields at Gardiner’s Riverbend Trails,..