Trail Running calendar near Windsor 2026-2027

The Gurney Lane 5K Snowshoe Race will take place in Queensbury on Saturday 17 January 2026. You can run 5 kilometers.

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.

CT123 is a point to point 123 mile ultramarathon across Connecticut, blending trails and backroads for a scenic, challenging adventure. Choose solo 200K or 100K or team relay options, and earn a buckle or medal plus a 2025 race tee.

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.

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.

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..

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 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.

TARC Wapack and Back in Ashburnham MA features 21.5, 43 and 50 mile out and back runs on the classic Wapack Trail. Rugged rocky singletrack, big climbs and sweeping views, plus aid stations and headlamp requirements for longer distances.

Run the Free Spirit 50K in Leyden, Massachusetts and enjoy a scenic New England ultramarathon. The course follows dirt roads past historic farms, leafy woods and an 1870s covered bridge for a rewarding, challenging day.

Run or walk the Ledge Rock Hill Wine Run 5k at Ledge Rock Hill Winery in Lake George on Sunday May 17 2026, a scenic vineyard course welcoming all paces. Enjoy a T shirt, collapsible wine glass and finisher medal while supporting Nik's Wish..

Explore Soapstone Mountain trails in Stafford Springs with a new half marathon that climbs past the fire tower or a fun 6K sampler open to walkers. Proceeds benefit Connecticut trail stewardship. The event is cupless so bring your own water..

Sharpen your trail skills at a three day Spring Training Camp in Oliverea NY. Expert coaching and guided runs on technical Catskill ridgelines include a 13 mile day with 5000 ft of climbing, plus lodging, meals and great camaraderie.

Tackle rugged single track and jeep roads in Keene, NH at the Drummer Hill Trail Races on May 23, 2026. Complete one to four 12.5k laps to choose your distance, enjoy aid stations and earn a drumstick finisher award.