Trail Running calendar near Pittsfield 2024-2025

The Tower Tag Challenge is an exciting running event taking place at Sleeping Giant State Park in Hamden, CT. Participants can choose between 8-hour and 4-hour options, racing along the Tower Trail, which features a scenic ascent to the Observation Tower. Each loop covers approximately 3.4 miles, wi..

Seth's Fat Ass 50K is an exciting running event taking place in Springfield, MA, at Forest Park. Participants can choose to complete one, two, or all ten loops of the 50K course, with a total time limit of seven hours to finish. The event promises a fun atmosphere and includes custom schwag for all ..

The West Rock Winter Fat Ass Extravaganza is an exciting running event held in Hamden, CT, featuring 1.6-mile loops around Lake Wintergreen for a duration of eight hours. Participants can enjoy a variety of refreshments, including pizza, soup, and snacks, while an aid station provides essential supp..

The Dar Snowshoe Scramble is a fun and low-key running event that offers participants the option to snowshoe or trail run, depending on snow conditions. The course is approximately 3.8 miles, with potential variations between 5k and 10k. The event emphasizes enjoyment over competition, with no forma..

The Frigus Snowshoe Festival, organized by the Endurance Society, is an annual winter sports event held at Moreau Lake State Park in Gansevoort, NY. Scheduled for February 1, 2025, the festival features a variety of race distances, including a challenging 60K ultramarathon, a 30K, a 15K, a 4.7-mile ..

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 Northern Nipmuck Trail Race is a 16-mile trail running event held in Union, Connecticut, at Bigelow Hollow State Park. Revived in 2022 after a hiatus, the race maintains a low-key atmosphere and a friendly community vibe. Participants navigate a scenic course along the Nipmuck Trail, with minima..

The Sleeping Giant Trail Runs is an exciting and challenging trail running event set in Hamden, Connecticut, featuring two race distances: a 25K and a 50K. The course showcases the diverse terrain of Sleeping Giant State Park, with over 30 miles of trails that include smooth carriage roads and techn..

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 Verkeerder Kill Falls. The event ..

The Jack Bristol Lake Waramaug Ultra Races, taking place on April 27, 2025, is a celebrated ultra-running event marking its 51st anniversary, making it the oldest ultra in Connecticut and the first 100K in the U.S. Participants can choose from three distances: 100K, 50 miles, and 50K, all set on a s..

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. 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 Dandelion Dash and Mushroom Mile is a community running event taking place in Hadley, MA, featuring a 5K trail run/walk and a 1-mile fun run. Scheduled for May 4, 2025, the event aims to engage participants of all ages, promoting outdoor activity and family involvement. Proceeds from the event s..

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 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 distance options: 21.5 miles, 43 miles, and 50 miles. The course features challenging terrain wit..

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

The Plattekill Mountain Race, scheduled for June 1, 2025, is an exciting running event held in Roxbury, NY, featuring a challenging 6.5-mile mountain race with a significant elevation gain of 3,500 feet. This race is designed for both seasoned athletes seeking a tough challenge and those training fo..

The IronHike Endurance Series - Spring 2025 takes place at Mohawk Mountain in Cornwall, CT, featuring a unique blend of hiking and trail running. Scheduled from June 5 to June 8, 2025, participants can choose from various events, including individual and team formats for distances ranging from 15 to..

The Drummer Hill Trail Races, set in Keene, NH, offers a variety of challenging distances including 50K, 37.5K, 25K, and 12.5K. Participants can choose how many laps of the 12.5K course they wish to complete, allowing for a customizable experience. The race features technical terrain with elevation ..