Trail Running calendar near Great Barrington 2026-2027

Join a friendly, informal 5 to 10k run or snowshoe on a roughly 10k course with loaner snowshoes available. Bring a spare pair to share, enjoy light refreshments, and team up for bragging rights and a shared baked treat.

Join the Frozen Heart 900, a free grassroots winter loop in Rockfall CT where runners take on a 15 hour challenge around a 2.2 mile trail loop. Self supported format with a heated meeting room for warming, so bring headlamps and carpool.

Join the Frigus Snowshoe Festival at Moreau Lake State Park for fun snowshoe races from a kids mile to a 60K on scenic winter trails. Snowshoes are required and all finishers get medals while top racers earn awards.

Tackle roughly 16 miles on the scenic, technical Nipmuck Trail in Union, Connecticut, running an out and back through Yale Myers Forest to Boston Hollow. Field capped at 100 with limited aid and no race day registration; proceeds support lo..

Run Sleeping Giant State Park on scenic, challenging trails with 25K and 50K options. Tackle runnable miles, rocky singletrack and a steep scramble to sweeping views, while supporting the park through registration proceeds.

Run rugged, technical trails at Bear Mountain with 10K or half marathon options and stunning Hudson Valley and NYC skyline views. Proceeds support the New York New Jersey Trail Conference; race day is Apr 4.

Run a scenic quarter marathon at West Hartford Reservoir on April 11, 2026, as the Hartford Track Club hosts a small, timed field limited to 150 runners. Enjoy chip timing, post race treats and a friendly, looped trail course.

Run or walk the John Jay Community Trail Race in Cross River through scenic wooded trails and rolling hills, with 5k, 4k walk and a Kids Jay Dash on the track. A family friendly community event that finishes on the John Jay Contest Field.

Run a scenic all terrain 5K through Stamford Museum and Nature Center, looping Bendel Pond and passing farm animals. Bring kids for a fun run with Petunia the Scottish Highland cow and support the museum.

Take on the Traprock 50 at Penwood State Park in Bloomfield, CT on April 18, 2026. Choose a rugged 50K of three rolling, rocky loops or a single 17K loop along technical single track and scenic forest roads. Bring your own cup.

Join the Brooklyn Cider House Spiked Apple 5K in New Paltz on April 19, 2026 for a chip timed run or walk. Enjoy a tee, cider pour, donut and a finisher medal that doubles as a bottle opener for a festive post race celebration.

Squatchywaska Mountainfest in Ellenville NY on April 25, 2026 is a rugged trail test on the Shawangunk Ridge with a 25K and a 10 mile option over steep climbs and technical singletrack. Field capped at 150 and proceeds benefit Run Wild.

Women focused trail run at Lake Mohegan offering a runnable 5K loop, a 10K two lap option and a 4 hour loop challenge. Expect scenic trails, medals for finishers and post race snacks; nonbinary runners are welcome.

Celebrate the 52nd Jack Bristol Lake Waramaug Ultra on April 26 in Kent Connecticut with 100K, 50 Miler, and 50K options on scenic rolling loops around the lake. Fast paved roads, four aid stations, and a friendly finish at Lake Waramaug St..

Enjoy a spring 10k trail race in Cross River, NY on April 26, 2026, winding through scenic park trails. Entry is by lottery with registration opening January 2, 2026, perfect for trail runners seeking a well organized challenge.

Tackle the rugged Seven Sisters Trail Race on May 2, 2026 along the Holyoke Range ridgecrest in Amherst, MA. This 12 mile out and back packs over 3,500 ft of climbing on technical singletrack with steep, rocky ledges for a true trail challe..

Run to Remember on May 2, 2026 in Red Hook NY offers scenic 5K and 10K trail runs plus a 5K walk through meadows, orchards and forest. Honor loved ones and enjoy community spirit with cash prizes for top finishers.

Take on Breakneck Point Trail Runs in Beacon, NY on May 3, 2026, with half and full mountain courses over rugged, technical trails, steep climbs, and sweeping views. Expect big elevation, aid stations, informal camping, and a lively trail c..

Blue 2 Blue Challenge is a tough 50K on New Haven's blue blazed trails, featuring rocky technical terrain and big climbs linking West Rock and Quinnipiac. Entry is by vetted waitlist and the race enforces strict cutoffs so come prepared.

Take on the Dandelion Dash 5K or the Mushroom Mile on The Hartsbrook School trails, with a virtual option available. Muddy, scenic terrain and proceeds support the school's Land Stewardship program.