Trail Running calendar near Southwick 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 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..

The Thacher Park Trail Running Festival, held annually at Thacher State Park in Voorheesville, NY, offers a scenic and challenging trail running experience. Participants can choose from four distances: 10K, half marathon (13.1 miles), marathon (26.2 miles), and an ultra 50K. The course features a sh..

The Old Goat Track Club XC Classic is a 5K cross-country race held at Water's Farm in Sutton, Massachusetts. Scheduled for August 24, 2025, it features separate Women's and Men's Open 5K races. The event serves as the first race in the USATF New England XC Grand Prix series and is part of the USATF..

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 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.

The Macedonia Trail Race, held annually in Macedonia Brook State Park in Kent, Connecticut, offers trail runners a unique and challenging experience with its lush forest trails, technical singletrack, and stunning viewpoints including Cobble Mountain, where runners can see the Catskill Mountains on..

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 an annual 5K trail run and walk held at the Oswegatchie Hills Nature Preserve in Niantic, Connecticut. The event features a scenic course that runs by Clark Pond and around the perimeter of the preserve, offering participants beautiful coastal forest views across more than 450 a..

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 Pisgah Mountain Trail Races, held in Pisgah State Park, Chesterfield, New Hampshire, feature two challenging trail distances: a 50K and a 23K. Organized by the Red Clover Rovers, this event serves as a fundraiser for the New Hampshire Special Olympics, with all profits supporting their mission...

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 All of the Above Trail Fest, held at Northfield Mountain Recreation Area in Massachusetts, is an inclusive trail running event welcoming queer, transgender runners, allies, and all participants regardless of athletic level. The festival features a longer 20-25k prediction run, a 5k untimed fun r..

The Angevine Farm Trail Festival is a scenic trail running event held in Warren, Connecticut, in the picturesque Northwest corner of the state. The festival features multiple race options including an 8-hour endurance run, a half marathon, and 5K races with a Canicross option for runners with dogs...

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,..