Trail Running calendar near Pittsfield 2026-2027

Point-to-point trail races on the Wapack Trail offering 21.5, 43 and 50 mile options over rocky, technical terrain with significant elevation gain; five aid stations, manual timing, drop bag service, and a strict no-refund registration poli..

A second annual 6k 3.8 mile cross country run at Bruynswick Winery in Gardiner, NY supporting the Ulster County SPCA. The day features music, a meet and greet with shelter animals, awards, and free children's dashes.

Spring Fling 600 in Southington, CT on May 9, 2026 features a 600 minute looped trail event and a 6 Mile race at YMCA Camp Sloper. Both events use chip timing and offer finisher medals and awards for top competitors.

A community event on May 9, 2026 featuring a Family Color Run and a 5K Trail Run at Hamden and New Haven YMCA locations. Registration runs from Feb 20 to May 8 with entry fees of $10 and $30; first 100 pre-registrants receive a Y giveaway.

A 5K trail run through the orchard at Indian Ladder Farms on May 10, 2026, with a hard cider mimosa provided after the finish and non alcoholic options; top 1st to 3rd place finishers aged 21 and over receive craft cider bottles.

A last person standing event on rugged Ragged Mountain in Berlin CT where runners repeat a roughly 3.11 mile loop each hour until one runner remains. Entry is limited to 55 and proceeds support local trail and youth running programs.

A dirt road 50k in Leyden, Massachusetts on May 16, 2026, with 4,200 feet of elevation change and a course that passes through forests, fields, and an 1870s covered bridge. Registration closes May 13 and there is no race-day entry.

A May race day on the Ashuwillticook Rail Trail offering a marathon, half, 8K and kids mile, with race shirts, finisher medals, aid stations, and proceeds supporting trail maintenance.

Trail running in Pittsfield State Park with 50K, 25K and a 5 mile course on single track and flowy forest trails. The event is organized by BURCS and benefits local animal rescue organizations.

A chip timed 5k at Ledge Rock Hill Winery in Lake George, NY, on a cross country style out and back course. Race swag includes a T shirt, a shatterproof collapsible wine glass and a medal, with age group awards and charity partner Nik's Wis..

A community 5K in Ellenville on May 17, 2026 that starts and finishes at Aroma Thyme Bistro, follows the base of the Shawangunk Mountains and the newly resurfaced Rail Trail, and finishes with a garden gathering; proceeds benefit local food..

New for 2026: an all-new Soapstone Mountain Half Marathon and a 6K Sampler in Stafford Springs, CT, both routed through Shenipsit Forest and past the Soapstone fire tower. The event is part of the Blue Blazed Trail Running Series and suppor..

A 3.5 mile trail run and walk at Woodtick Recreation Area in Wolcott CT on May 17, 2026. Proceeds support the Wolcott Cross Country Teams and division winners receive medals, with race entry including a free $10 pass to the CT Food Truck Ba..

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 using a 12.5K loop that can be repeated for 12.5K, 25K, 37.5K, or 50K. The course is technical single track and old jeep roads with aid stations, drop bag access, and portable toilets.

A road half marathon around Mine Hill Distillery in Roxbury CT featuring mixed paved and dirt roads, a long climb in the first half and a mostly downhill return. Three aid stations support a cupless hydration policy and finishers receive a..

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.

Test your endurance at the Ascutney Mountain Run in Vermont. This 3.7 mile uphill race climbs 2,300 vertical feet along a paved auto road to a scenic mountain summit finish.

Rise of the Obstacles in Wallkill, NY on May 30-31, 2026 features adult and kids obstacle races from a 100 meter sprint to a 2 km multi-lap course, plus a Teddy Bear Crawl nonprofit and a 3D printing fundraiser for youth programs.

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.