Trail Running calendar near Guilford 2024-2025

The West Rock Winter Fat Ass Extravaganza is an exciting running event taking place 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, grilled cheese, and snacks, while an aid station..

The Cross Island 20 Miler Trail Run is an annual event organized by the Long Island Trail Running Club, taking place on December 28, 2024, in Massapequa, NY. This unique trail run spans from Long Island's South Shore to the North Shore, attracting enthusiastic runners who enjoy the camaraderie of li..

The Squatchy Onesiefest 5K is a unique winter trail running event scheduled for February 8, 2025, at the Ramapo Valley County Reservation in Mahwah, NJ. Participants are encouraged to wear their favorite onesies for a fun and memorable experience. The event features a scenic "lollipop" course that r..

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, taking place on March 29, 2025. Organized by the Shenipsit Striders, the race features a scenic course that traverses the Nipmuck Trail and the Yale-Myers Forest. Participants can expect a challenging terrai..

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..

Big Bear Squatch North is an exciting trail running event set to take place in Bear Mountain, NY, featuring a variety of distances ranging from 5K to 50K. The course has undergone several reroutes in previous years due to storm damage, and the organizers are currently assessing the trails for the 20..

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..

Shore2Shore is an exciting running event taking place in East Islip, NY, featuring a scenic 50K and 25K race along the beautiful Suffolk County Long Island Greenbelt Trail. Participants will experience a point-to-point course that starts at Sunken Meadow and finishes at Heckscher State Park, with fu..

The Sterling Squatch Half Marathon, part of the Squatchywaska Mountainfest, offers participants a unique trail running experience through the stunning landscapes of the Shawangunk Ridge. Runners can choose between two challenging courses: a 10-mile route and a 25K course, both featuring significant ..

The Jack Bristol Lake Waramaug Ultra Races, taking place on April 27, 2025, marks the 51st anniversary of this historic event, known as the oldest ultra race in Connecticut and the first 100K in the United States. Participants can choose from three distances: 100K, 50 miles, and 50K, all set on scen..

Leatherman's Loop is a popular 10k trail race held annually in Cross River, New York. The event is known for its scenic course and community spirit, attracting participants of all ages, from 7 to 107. Due to its popularity, entry is determined through a lottery system.The registration fee includes t..

The Forgotten Forest Ultra Run, taking place in Stratford, CT, is a unique 9-hour trail running event set in the scenic Roosevelt Forest. Participants can choose to run, jog, hike, or walk on a well-marked loop trail featuring an elevation gain of approximately 131 feet per loop. This friendly compe..

The 7 Sisters Trail Race will take place in Amherst on Saturday 3 May 2025. You can run between 12 and 12 miles.

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. The course features a diverse range of terrain, including short climbs..

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 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. Scheduled for May 4, 2025, the event aims to support The Hartsbrook School's unique programming, which includes land stewa..

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 Spring Run The Farm event will take place at Muscoot Farm in Katonah, NY, on May 18, 2025. This exciting running event features a 5-mile trail race for participants aged 6 and older, along with two kids' races: one for ages 7-12 and another for children aged 6 and under. The event aims to showca..