Trail Running calendar near Great Barrington 2026-2027

A classic 16-mile trail run on Connecticut's Nipmuck Trail, known for its technical terrain and old-school vibe. Organized by the Shenipsit Striders, the event supports local trail stewardship. Registration is capped and no race day signups..

Course and Distances The Sleeping Giant Trail Runs take place at Sleeping Giant State Park in Hamden, Connecticut. The event offers two distances: 25 km: A single loop with over 3,000 feet of vertical gain. 50 km: Two loops of the 25 km co..

Tackle the rugged trails of Harriman State Park in this mountain trail run. Choose between a challenging 10K with 1,400 feet of climb or a half marathon with over 2,600 feet. The event supports local trail maintenance and includes a rucking..

Course and Distance The Run Across CT 123 is a point-to-point ultramarathon that travels coast-to-coast across Connecticut, covering approximately 123 miles (200K). The route passes through 25 towns, starting in East Thompson and finishing..

The Bimbler's Bash is a popular annual 10K trail run through the technical, rocky paths of Guilford's Westwoods. This entirely off-road event supports local land conservation and is known as a major single-distance race in Connecticut.

Run a unique quarter marathon distance on the paved trails of West Hartford Reservoir. This chip timed 6.55 mile race features a two loop course with post race treats and age group awards.

A fast, point-to-point half marathon descending from Slingerlands to the Hudson River in Albany. The course features paved rail trails and offers amenities like live tracking, gear check, and a post-race celebration. A free shuttle bus mana..

Experience a community trail event in Cross River featuring a competitive 5k race, a scenic 4k walk, and a 200m kids dash. Explore the wooded hills of the John Jay Community Trail ending at the campus contest field.

Run through a scenic nature center featuring farm animals and wooded trails. This all terrain event in Stamford offers a unique 5K course and a fun run for children ages five and up.

The 11th Annual F.O.R 5k Trail Race takes runners through the scenic McDonald Nature Preserve in Wilbraham. This family-friendly trail run supports the local parks' maintenance fund.

The Traprock 50 features a rugged 50K and a 17K trail race on the rocky, rolling loops of Penwood State Park. It's a cupless event with chip timing, organized by volunteers to benefit local conservation groups. Runners should be prepared fo..

Run or walk through the scenic orchards of New Paltz at this chip timed 5k event featuring homemade donuts and fresh cider for all finishers.

Event Overview The Squatchywaska Mountainfest is a trail running event with two distances: a 25K (noted as closer to 17 miles) and a 10-mile race. Both courses follow a lollipop format through Minnewaska State Preserve on the Shawangunk Rid..

The Lake Mohegan Women's Trail Race is a women's-only trail event in Fairfield, CT. Runners can choose from a 5K, 10K, or a 4-hour challenge on the runnable trails around the lake. The event aims to welcome both newcomers and experienced tr..

The Grafton 15K is a spring trail race through the technical and muddy terrain of Grafton Lakes State Park. The 9.3-mile course features 900 feet of elevation gain, starting and finishing at the park's beach.

The Leatherman's Loop is a classic 10k trail race held each spring at Ward Pound Ridge Reservation. Entry is secured via a lottery system, with no same-day registration. It's part of a series of trail events including Run the Farm and Raven..

Try the Trail is a youth trail run for ages 4 to 16 at Katonah Memorial Park. Kids can choose between a half-mile or one-mile course on scenic, easy-to-follow trails. It's a family-friendly event focused on outdoor activity.

A 12 mile out and back trail race on the Holyoke Ridge near Amherst MA featuring technical singletrack, over 3,500 feet of ascent, a 500 runner cap and a waitlist when full.

The A Run to Remember will take place in Red Hook on Saturday 2 May 2026. You can run between 5 and 10 kilometers.

Rock The Ridge is a 50-mile endurance challenge set in the scenic Shawangunk Mountains of the Mohonk Preserve. The event also features a trail marathon and relay options, all while raising funds to support the preserve's conservation and ed..