Trail Running calendar near East Hampton 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..

Trail races at Watuppa Reservation in Fall River on May 9, 2026, featuring grassy fire lanes, winding single track and aid stations each lap. Distances offered are 10K, 30K and 50K.

A spring 10K trail race on Block Island with varied terrain including dirt roads, stone walls, coastal track views, and a steep double tiered climb near mile four. Start and finish are at the Block Island School.

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 dog friendly 5K and a 2.6 mile walk at Borderland State Park on May 9, 2026 to benefit School on Wheels of Massachusetts. The event features refreshments, pup cups, kids pupsicles and free t shirts for early registrants.

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.

Run the Forgotten Forest 9-Hour Ultra on a challenging 2.2-mile loop trail in Roosevelt Forest. This event is a perfect training ground for longer ultras, welcoming runners and hikers of all paces. With a small field of just 50 participants..

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.

Run or walk a 5k on the Southern New England Trunkline Trail in Franklin. This event supports the development of an abandoned rail bed into a multi use path connecting local communities.

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.

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..

Tough Tiger is an obstacle course event at Hampden Meadows School in Barrington, RI offering a 1.5 mile loop and a shorter adaptive course, with T shirts for early registrants, a raffle, and electronic timing.

Trail marathon and 15-mile trail race at Bethpage State Park on May 17, 2026. Registration opens Feb 23 and a portion of proceeds supports the Long Island Greenbelt Trail Conference.

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.

Experience a refreshing spring trail run or walk through the scenic paths of Blydenburgh County Park. Enjoy a 5K course featuring dirt roads and wooded trails followed by delicious refreshments and professional finish line photos.