Trail Running calendar near Pittsfield 2025-2026

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..

Squatchywaska Mountainfest is an exciting trail running event taking place in Ellenville, NY, featuring two challenging courses: a 25K and a 10-mile race. Participants will navigate stunning mountain singletracks, experiencing breathtaking views of the Catskills and the iconic Verkeerder Kill Falls...

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 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 Breakneck Point Trail Runs, organized by Red Newt Racing, is a challenging trail running event set to take place on May 4, 2025, in Beacon, NY. Participants can choose between a half marathon (13.1 miles) and a full marathon (26.4 miles), both featuring significant elevation gains and technical..

The Blue 2 Blue Challenge is a demanding 50K trail race set in New Haven, Connecticut, known for its challenging terrain and technical trails. This event, which runs along the Regicides and Quinnipiac Trails, features over 6,350 feet of elevation gain, making it one of the toughest races in the stat..

The Spring Fling 600 is an annual trail running event organized by the CT Trailmixers, taking place at YMCA Camp Sloper in Southington, CT. This year marks the eighth edition, featuring two race options: a 600-minute challenge where participants can run as many loops as they wish on a roughly three-..

The Bruynswick Winery Run for UCSPCA is a 4.5-mile cross-country race organized by the Shawangunk Runners, taking place at the scenic Kiernan Farm/Bruynswick Winery in Gardiner, NY. This event aims to support the Ulster County SPCA, which is facing increasing demands due to the rising number of anim..

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 "Run Like A Mother" 5K Trail Run, organized by the Franklin Elementary School PTO, is a family-friendly event taking place at Giddings Park in North Franklin, CT. This Mother's Day-themed race celebrates the incredible role of mothers and is open to participants of all ages, including a special..

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 Run Ragged Last Person Standing event, hosted by the CT Trailmixers, is an exciting endurance race set in the rugged terrain of Ragged Mountain, Berlin, CT. Participants will tackle a challenging 3.11-mile loop, with one hour to complete each lap. The race continues until only one runner remains..

The Mayfly Ultra is an exciting running event taking place in Stony Creek, NY, featuring a challenging 49K ultra marathon and a 27K mini run, along with a relay option for teams of four. Set against the stunning backdrop of the Adirondack Park, participants will navigate both paved and unpaved roads..

The Free Spirit 50k is an ultra-running event set in the scenic landscapes of New England, featuring a challenging dirt road course with a total elevation change of 4,200 feet. Participants will enjoy breathtaking views as they traverse through forests, fields, and even cross a historic covered brid..

The 16th Annual Farmington River Run 5K Trail Race is scheduled for May 18, 2025, at Winding Trails in Farmington, Connecticut. This scenic race takes place on a designated 5K trail within a 300-acre area surrounding Walton Pond. Participants can compete for awards in various categories, including o..

The Soapstone Mountain Trail Races, taking place on May 18, 2025, in Stafford Springs, CT, features two scenic races: a 25K and a 6K "Sampler." Both courses wind through the picturesque Soapstone Mountain area and Shenipsit Forest State Park, offering a mix of challenging terrain and beautiful lands..

The Mine Hill Half Marathon, organized by Steep Endurance, is touted as one of the toughest road half marathons in Connecticut. Set against the picturesque backdrop of the Mine Hill Distillery in Roxbury, participants will enjoy stunning views of farms and fields while navigating a challenging cours..