Trail Running calendar near Holyoke 2025-2026

The Spring on the Trails Endurance Runs is an exciting annual event held in Lagrangeville, NY, featuring timed races of 3, 6, and 12 hours on a scenic 5k trail loop with approximately 250 feet of elevation gain per lap. Participants aim to complete as many loops as possible within their chosen time..

The Enchanted Forest Ultra Run is a captivating 6-hour ultra event taking place in Roosevelt Forest, Stratford, CT. Participants can run or hike a 2.3-mile loop trail, aiming for as many miles as possible within the time limit or striving for the 50K milestone. This event is suitable for both novice..

The Northern Nipmuck Trail Race is a 16-mile trail running event held in Union, Connecticut, organized by the Shenipsit Striders. Revived in 2022 after a hiatus, the race maintains a friendly, low-key atmosphere, attracting runners of all levels. The course traverses the Nipmuck Trail, featuring tec..

The Sleeping Giant Trail Runs, set in the iconic Sleeping Giant State Park in Hamden, CT, promises to be one of the toughest trail races in the Northeast. Participants can choose between a challenging 25K or a grueling 50K course, featuring over 30 miles of diverse terrain, including smooth carriage..

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 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 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 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 TARC Spring Classic, organized by the Trail Animals Running Club, is a trail running event set to take place at the Jericho Town Forest in Weston, Massachusetts, on April 26, 2025. Participants can choose from various distances, including 10K, Half Marathon, Marathon, and 50K. The course feature..

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..

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..

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..

The Blue 2 Blue Challenge is a demanding 50K trail race set in New Haven, Connecticut, known for its challenging terrain and technical trails. Participants will navigate some of the toughest trails in the state, including the Regicides and Quinnipiac Trails, with a total elevation gain of approximat..

The Ansonia Trails 5K is a running event taking place in Ansonia, CT, designed for participants of the 169 Society. This second annual race features a unique course consisting of two laps around a 1.55-mile loop, making it slightly over or under a traditional 5K distance. Limited to 50 runners, the..

The TARC Wapack and Back is a challenging trail running event organized by the Trail Animals Running Club, taking place along the scenic Wapack Trail in Ashburnham, Massachusetts. Participants can choose from three distances: 21.5 miles, 43 miles, and 50 miles, with the course featuring rocky ledges..

The Tails & Trails State Forest Run, scheduled for May 17, 2025, in Pittsfield, MA, features three race distances: 50K, 25K, and a 5 Miler. This event supports local animal rescue nonprofits, including Red Robin Song Animal Sanctuary, No Paws Left Behind, and Berkshire Bird Paradise, Inc. Participan..

The Dash For Dane & Family Day is an annual event held at Powisset Farm in Dover, MA, designed to honor the memory of Dane and support important causes. The event features a 5K Trail Run/Walk, a 1K Kids Fun Run/Walk, and various family-friendly activities such as magic shows, crafts, and live music...