Trail Running calendar near Stratford 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 Mohawk Mountain Race, held at Mohawk Mountain Ski Area in Cornwall, Connecticut, offers a challenging trail running experience with 5K, 10K, Half Marathon, and Marathon distances. The course features steep ascents and descents on ski mountain trails, including the Wildwood, Timber, Pine, Laurel,..

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 42 kilometers.

The Tom Centinaro Memorial "Dam" Race will take place in Waterbury on Saturday 18 October 2025. You can run 3 miles.

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

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 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 Bimblers Bluff 50K is an off-road trail race held in southern Connecticut, starting at Guilford Lakes School in Guilford. The course traverses several interconnected woodland preserves, featuring rolling forest roads and single-track trails that can be extremely rocky, offering a challenging tes..

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 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 Fall Back Into The Trails Series, held at Red Wing Recreation Area in Lagrangeville, NY, offers challenging trail races including a 100K, 50K, and 10K. The 50K consists of five 10K loops with approximately 5,000 feet of elevation gain, while the 100K features ten 10K loops with about 1,000 feet..

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 that includes single track and farm trails, offering a scenic and community-focused atmosphere. Participants can cho..

The Stonington Vineyards Wine Run Turkey Trot 5k is a festive running event held at Stonington Vineyards in Stonington, Connecticut. This chip-timed 5k features a two-lap cross-country style course that winds through vineyard lanes, offering scenic views and some uneven terrain suitable for both run..

The Pocantico Hills Marathon, held in Sleepy Hollow, NY, offers both marathon and half marathon distances through Rockefeller State Park. The single-loop courses feature rolling hills with scenic views of the Hudson River and Palisades, passing fields, stone walls, bridges, lakes, streams, forests,..

The Raven Rocks 10k Trail Run is an annual challenging trail race held at Ward Pound Ridge Reservation in Cross River, NY. The course features rugged terrain with rocky climbs, ridgeline trails, hilly meadows, and ravines, ascending to the park's two highest points: Raven Rocks Overlook and the Fire..

The NSRF 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 a grassy polo field and winds through scenic, mostly flat, beginner-friendly trails with a true cross-country feel. Participants enjoy post-race refreshme..

NYC Trail Mix is an annual ultra trail running event held in Staten Island, New York, featuring distances of 50 miles, 50K, and a half marathon. The course showcases over 35 miles of trails through the greenest parts of New York City, including Blood Root Valley, High Rock Park, La Tourette Park, an..

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 at Tarrywile Park in Danbury, Connecticut, is a challenging trail race known for its significant elevation gain of nearly 3,000 feet and technical Northeast single-track terrain. The course offers stunning views of Danbury and the park's tranquil lakes. The event fe..