Trail Running calendar near Simsbury 2025-2026

Big Bear Squatch North is an exciting trail running event taking place at Harriman State Park in Bear Mountain, New York. Scheduled for April 5, 2025, this challenging race features a half marathon and a 10K, both showcasing the park's rugged terrain, steep climbs, and stunning vistas. Participants..

The Mt. Toby Ultra is a trail running event offering three distance options: 13k, 24k, and 50k, each showcasing the scenic beauty of Mt. Toby.The race serves as a fundraiser for Girls on the Run of Western Massachusetts, promoting joy, health, and confidence among girls through running. Participants..

The Run for the Rescue 5K Trail Run/Walk is scheduled for April 5, 2025, at Blydenburgh County Park in Hauppauge, NY. This dog-friendly event encourages participants to bring their leashed pets along for the run. The course features a mix of trails suitable for all experience levels. Registration op..

The Farm & Forest All-Terrain 5K & Kid Fun Run is an exciting outdoor running event scheduled for April 6, 2025, in Stamford, Connecticut. Participants will enjoy a scenic 5K course that begins at the Fedele Family Plaza and winds through Heckscher Farm, featuring various animals and beautiful lands..

The John Jay Community Trail Race is a competitive running event taking place in Cross River, NY, featuring a 5k race, a 4k Jay Walk, and a Kids Jay Dash. The 5k race is set on the newly developed John Jay Community Cross Country Trail, which includes challenging wooded terrain. The 4k Jay Walk offe..

The "4 in the Forest" event is a trail running race taking place in Irvington, NY, featuring a challenging 4-mile course through the scenic Irvington Woods. Participants can look forward to a memorable experience, complete with a custom-designed race patch and medal. The event encourages community i..

The 10th Annual F.O.R 5k Trail Race will take place at the McDonald Nature Preserve in Wilbraham, MA. This family-friendly event encourages participants of all ages to enjoy the outdoors while supporting the Recreation Maintenance Fund for local parks. The race features a scenic course rated easy to..

The Brookhaven Trail 15K and 4 Mile Trail Run is set to take place at Brookhaven State Park in Wading River, NY. This popular event features a challenging course that includes various trail conditions, from single-track paths to sandy sections, all within the scenic woodlands of Suffolk County. Part..

The Grafton 15K is an exciting running event set in the scenic Grafton Lakes State Park, featuring a challenging course that spans approximately 9.3 miles with an elevation gain of 900 feet. This spring race is designed to be accessible for new trail runners, offering technical yet runnable trails...

The Traprock 50 is a challenging trail running event held at Penwood State Park in Bloomfield, CT, featuring two race distances: a 50K and a 17K. The course consists of approximately 10.5-11 miles per loop, with the 50K requiring three loops and the 17K one loop. Runners will navigate a mix of techn..

The Lake Mohegan Trail Race is a women's only trail running event held in Fairfield, CT, organized by Steep Endurance. Aimed at promoting trail running among women, the event typically sees 30-40% female participation, with over 125 runners in 2024. The race features three distance options: a 5K, a..

The Radish Rambler 5k at White Barn Farm is a fun and engaging trail run/walk/hike set in the scenic conservation land of Wrentham, Massachusetts. Scheduled for April 26, 2025, this event welcomes participants of all ages and skill levels, marking the opening day of the farm and an Earth Day celebra..

The Jack Bristol Lake Waramaug Ultra Races, taking place on April 27, 2025, is a celebrated ultra-running event in Connecticut, marking its 51st anniversary. This historic race features three distances: 100K, 50 miles, and 50K, all set around the scenic Lake Waramaug. Participants can expect well-st..

Leatherman's Loop is a popular 10k trail race held annually in Cross River, NY, attracting participants of all ages from 7 to 107. The event is known for its scenic course and community spirit, and entry is determined through a lottery system due to high demand. The registration fee includes the par..

The Conquer The Trail 5k is an annual running event celebrating its 10th year, taking place at Mercy University in Dobbs Ferry, NY. This year, the race will feature a flat and fast out-and-back course along the Old Croton Aqueduct Trail, with a single hill before the finish. Proceeds from the event..

The Forgotten Forest Ultra Run is a unique trail running event held in Roosevelt Forest, Stratford, CT. Scheduled for May 3, 2025, this 9-hour ultra trail race invites participants of all levels, including runners, joggers, hikers, and walkers, to complete as many miles as they can on a well-marked..

The 7 Sisters Trail Race is an exciting running event that features a series of wave starts based on anticipated finish times, ensuring a well-organized experience for participants. Runners are required to carry their own water, as the race is cupless, promoting sustainability. The event is capped a..

The Bear Mountain Trail Challenge is an exciting running event held at Bear Mountain State Park, located just an hour from New York City. Participants can choose from three race distances: a 50K, a half marathon (21K), and a 10K, all set against a backdrop of scenic trails that feature diverse terra..

A Run to Remember is a community-focused running event taking place at The Farm Trails at Greig Farm in Red Hook, NY. Scheduled for May 3, 2025, the event features a 5K Trail Run and a 5K Walk, designed to honor loved ones who have passed away while promoting health and togetherness. Participants ca..

The Dandelion Dash and Mushroom Mile is a fun running event taking place in Hadley, MA, featuring a 5K trail run or walk and a 1-mile race suitable for participants of all ages. This event aims to support The Hartsbrook School's unique programming, which includes land stewardship and sustainable pra..