Trail Running calendar near Woodbridge 2025-2026

The Paine to Pain Trail Half-Marathon is a distinctive trail race held in Westchester County, New York, starting at the historic Thomas Paine Cottage in New Rochelle and finishing at New Rochelle High School. This 13.1-mile single-loop course traverses the woods and trails of five different parks, o..

The Never Stop Running Foundation Great Pumpkin Dash Trail 5K is a scenic trail run/walk held at Blydenburgh County Park in Smithtown, NY. Scheduled for October 12, 2025, this event features a 5K course through shaded trails combining dirt roads and hard-packed paths with some sandy areas, suitable..

The Mt. Tom Trail Race, held within Mt. Tom State Park in Massachusetts, offers runners a challenging experience amid stunning fall foliage.Participants can choose from a solo 25k race with 3,600 feet of elevation gain, a 2-person 25k relay, or a solo 10k, all on rugged single-track hiking trails. T..

The Tackle the Trail - Pomfret, CT will take place in Pomfret on Saturday 18 October 2025. You can run between 10 and 26 miles.

The Castle to River Run in Garrison, NY, is a scenic running event held in the historic Hudson Valley, featuring a half marathon and a 5K race, along with a kids fun run. The half marathon course winds through Hudson Highlands State Park, passing the historic Osborn Castle and offering a mix of sing..

The FALL Run The Farm is a 5-mile trail race held at Muscoot Farm in Katonah, New York. Scheduled for October 19, 2025, the event features a main 5-mile race for participants aged 6 to 108, along with two kids' races: one for ages 7-12 and another for children 6 and under. The race showcases the sce..

The Bimblers Bluff 50K is an off-road ultramarathon held in southern Connecticut, starting at Guilford Lakes School. The course traverses several interconnected woodland preserves, featuring rolling forest roads and single-track trails that can be extremely rocky. Unlike many ultras, the route does..

The Big Bear Squatchtoberfest is a challenging trail running event held at Harriman State Park in Tuxedo, New York. Organized by Sassquad Trail Running in partnership with the New York-New Jersey Trail Conference, it features a half marathon (13.1 miles) and a 10K race. The courses are technical wit..

The Book It for Books 10k is a charitable running event held at Lake Accotink Park in Springfield, Virginia. The race features a 10k course that combines mostly trail running with some paved sections, including out-and-back routes on both the north and south sides of the lake. It benefits Reading is..

The Grills Trail Run, hosted by the Westerly Track & Athletic Club, takes place at Grills Preserve in Westerly, Rhode Island. Scheduled for October 25, 2025, it features two race distances: a 10-mile and a 10K. Both courses start and finish at Grills Preserve, showcasing scenic trails with about 80%..

The Fall Back Into The Trails Series is an annual trail running event held at Red Wing Recreation Area in Lagrangeville, NY. The 2025 edition features three race distances: a challenging 100K (10 loops of 10K each with about 1000ft elevation gain per lap), a 50K (5 loops of 10K with approximately 50..

8 Hours at the Farm is a trail running event held at Gurski Farm/Williams Park in Brookfield, Connecticut. The race features a rolling country course with an approximately 4-mile loop combining single track and farm trails, offering a scenic and community-focused atmosphere. Participants can choose..

The Pocantico Hills Marathon and Half Marathon take place in Rockefeller State Park, Sleepy Hollow, NY. These scenic single-loop courses feature rolling hills with picturesque views of the Hudson River and Palisades. Runners pass through fields, stone walls, bridges, lakes, streams, forests, and gra..

The Raven Rocks 10k Run is an annual trail race held at Ward Pound Ridge Reservation in Cross River, NY. Known for its challenging course, the race features rocky climbs, ridgeline trails, hilly meadows, ravines, and the scenic site of the former fire tower, offering runners great views. The event f..

The Never Stop Running Foundation Long Island Turkey Trail Trot 5K is an annual family-friendly run/walk held at Bethpage State Park in Bethpage, NY. The course starts on the open polo field and winds through scenic, mostly flat, beginner-friendly trails with a true cross-country feel. Participants..

The Li'l Rhody Runaround Trail Run is held at Burlingame State Park in Charlestown, Rhode Island. It features two trail running events: an 8-mile and a 4-mile course, both winding around the scenic Watchaug Pond. This race is part of the WTAC Fall Trail Race Series, offering a 10% discount for parti..

The Tarrywile Half Marathon, held in Danbury, Connecticut's Tarrywile Park, is known as one of the toughest trail half marathons in the region. Covering nearly 3,000 feet of elevation gain, the course features technical Northeast single-track trails with rocky, rooty, and hilly terrain. Runners enjo..

The Fall Fling 400 is an annual trail running event hosted by the CT Trailmixers at YMCA Camp Sloper in Southington, Connecticut. It features two main races: a 400-minute timed trail race where participants complete as many loops as possible on a roughly two-mile course with rolling hills and varied..

The Roxbury Thanksgiving Day Charity Race is a 5K event held annually in Roxbury, Connecticut. Scheduled for Thanksgiving Day, November 27, 2025, the race takes place at the Everett B. Hurlburt Community Park located at 18 Apple Lane.Participants run a 3.1-mile course, offering a community-focused a..

The 2025 Never Stop Running Foundation Leftover Turkey Trot 5K is a festive run/walk event held at Bethpage State Park in Bethpage, New York. Participants enjoy a scenic course starting on a grassy polo field and winding through mostly flat, beginner-friendly soft trails with a true cross-country fe..