Trail Running calendar near Lenox 2026-2027

A last person standing loop race on Ragged Mountain where runners repeat a roughly 3.11 mile loop and must finish each lap within one hour; entrants are eliminated if they fail to start or finish a lap, continuing until a single finisher re..

The Free Spirit 50K is a scenic ultra on the dirt roads of Leyden, Massachusetts. The route passes historic farms, forests, and a vintage covered bridge, offering a classic New England countryside experience.

Annual May races on the Ashuwillticook Rail Trail offering marathon, half and 8K distances starting and finishing at the Adams Visitors Center. Proceeds support the rail trail and a municipal fund for the City of Pittsfield.

Tails & Trails State Forest Run in Pittsfield State Park on May 16, 2026 features 50K, 25K and a 5 mile loop of single track, pine forests and mountain bike style trails while supporting local animal rescues.

Experience a scenic trail run through the meadows and forests of Muscoot Farm. Choose from the 5 mile course or youth races and receive vouchers to spend at the local farmers market.

Event Overview The Ledge Rock Hill Wine Run 5K takes place at the Ledge Rock Hill Winery in Lake George, New York. The event features a 5K distance, which is open to participants aged 1 to 99. It is a timed race, with professional timing an..

Celebrate a Hudson Valley tradition dating back to 1983 with the Run Like The Wind 5K in Ellenville. This scenic course runs along the Shawangunk Mountains and features a section on the newly resurfaced Rail Trail. All event proceeds suppor..

Trail races at Soapstone Mountain in Stafford Springs, CT include a new half marathon and the Jerry Stage 6K Sampler. Courses run on the blue blazed Shenipsit Trail through Shenipsit Forest with on course aid for the half marathon.

Run a 3.5-mile trail race in Wolcott, CT. The event supports the local cross country teams. Your entry includes access to the CT Food Truck Battles Festival afterward.

A community campus race in East Haddam with a 1.75 mile loop, kids races on the soccer field, water stops and reused trophy awards. The course is mainly packed dirt with hills and a fast downhill finish.

A one-day return of the Somers Summer 5K on May 17, 2026 at Field Road Park; entry is free and registration runs from August 28, 2025 to May 16, 2026. Proceeds support improvements to the park fitness trail.

Trail races in Keene, NH on a revised, technical course where runners choose how many 12.5k laps to run. Natural single track and jeep roads, cupless aid stations, parking at Fuller Elementary School, and drumstick awards.

Mine Hill Half Marathon is a 13.1 mile road race in Roxbury, Connecticut, with start and finish at Mine Hill Distillery. The course passes farms, fields and scenic vistas and includes a post-race gathering at the distillery.

Experience a 5K cross country run or walk through the mowed trails of Peach Hill Park. Reach the highest point in Poughkeepsie for panoramic views and enjoy post race snacks and awards.

Rise of the Obstacles in Wallkill NY on May 30-31 features adult and kids obstacle races including a 100 m sprint, a two-lap endurance course, and kids 50 m and 1 km heats. Events include finisher medals, age-group awards, a Teddy Bear Craw..

A running event in Granville on May 30, 2026: a relatively flat 5k along the rail trail finishing on the footbridge over the Mettowee, plus a kids 1k. Registration opens March 26; 5k fee $25, kids run free.

A choose your own adventure trail event at Chesterfield Gorge Reservation on a rolling jeep road alongside the river. Multiple ultra and shorter distances are offered, with a 30 hour window for ultras, water and manned aid stations, and non..

Multi-day elevation based endurance events at Mohawk Mountain in Connecticut, June 4 to 7, 2026. Solo, Trail Buddy and Trail Family formats cover timed events from a 12-hour 15-mile option up to 84-hour 152+ miles with large elevation gain.

Point to point trail ultramarathon along the New England Trail with 112 mile and 50 mile options through Connecticut. Entrants must donate to the Connecticut Forest and Park Association and arrange their own crew and navigation support.

Experience a timed 5K trail run or walk through the scenic woods and fields of the Van Vleck Farm and Nature Sanctuary. Enjoy live music and food trucks at this annual community event in Woodbury.