Trail Running calendar near Simsbury 2025-2026

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 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 Race for DFL is a unique "last runner standing" backyard ultra event held at Kenty’s Farm in Winchendon, Massachusetts. Participants run a 4.1666-mile loop every hour on the hour, continuing until only one runner remains. The course features a mix of terrain including grassy fields, trails, crus..

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 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. The challenging course features nearly 3,000 feet of elevation gain and technical Northeast single-track terrain. Runners enjoy stunning views of Danbury and the park's t..

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 event where participants run as many loops as possible on a roughly two-mile trail course, and a 4-mile race consisting of..

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..

Rob's Trail Run Edition is a trail running event held in Woodbury, New York, at Stillwell Woods Preserve. Scheduled for November 30, 2025, the event features two main races: a 5K Adult Trail Run for participants aged 19 and older, and a 5K High School or Youth Trail Run for those 18 and under. The c..

The Tower Tag Challenge is a trail running event held at the iconic Sleeping Giant State Park in Hamden, Connecticut. The race features a simple yet demanding course on the Tower Trail, a mostly smooth carriage road that ascends over 600 feet in 1.5 miles to the park's Observation Tower, offering st..

The Frosty Forest 5K is a trail running event held in Roosevelt Forest, Stratford, Connecticut. This 5K race offers participants a chance to escape the roads and enjoy a scenic course through nature. Runners, joggers, hikers, and walkers are all welcome, with a requirement of some trail experience.P..

The Sleeping Giant Trail Runs, held at Sleeping Giant State Park in Hamden, Connecticut, is a challenging trail running event known as one of the toughest in the Northeast. The race offers two distances: a 25K loop with over 3,000 feet of vertical gain and a 50K option for runners who complete two l..

Run Across CT is a challenging ultramarathon spanning 123 miles across Connecticut, starting in East Thompson and finishing at the Wakeman Boys & Girls Club in Southport. The point-to-point course traverses 25 towns, combining approximately 57 miles of well-maintained trails with scenic backroads an..

Big Bear Squatch North is a challenging trail running event held at Harriman State Park in Bear Mountain, New York. Featuring a half marathon and 10K races, including a unique rucking division with lightweight (15 lbs) and heavyweight (30 lbs) categories, the course offers rugged, technical trails w..

The John Jay Community Trail Race, held in Cross River, NY, is a competitive 5k run on the newly developed John Jay Community Cross Country Trail. The course begins on the lower fields of the John Jay Campus, quickly entering challenging, hilly wooded trails near the middle and high schools, and fin..