Trail Running calendar near North Fork 2026-2027

Trail Race REXTRAVAGANZA on May 9 at Clausland Mountain in Orangeburg features 3.75, 7.5, and 11.25 mile trail options, supports mental health and sobriety, and includes aid stations, a medal, and an optional T-shirt.

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 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.

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..

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.

A four mile cross country race in Riverdale and Van Cortlandt Park with an informal kids fun run, finisher hat, awards for top finishers and masters, and post race refreshments; proceeds benefit the FDNY Foundation.

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.

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..

A four mile road and trail race in Forest Park with start and finish at Victory Field track. The event is limited to 500 entrants, includes chip timing, technical shirts for pre-registrants, finisher medals, cash awards and age group trophi..

Six 5K cross country races take place at Van Cortlandt Park from May 28 to July 30, 2026, on the classic Tortoise and Hare course. The final three evenings include free half mile kids runs, weekly awards and post race raffles.

ENDURE Last Man Standing in Bethpage State Park asks runners to repeat a fixed 4.2 mile loop each hour; finish within the hour to continue. Laps continue with progressively shorter cutoffs until one runner remains or the event window ends.

A timed 5K trail race at Coogan Farm in Mystic, running through meadows, woods, and fields, with limited entry, tiered fees, an awards ceremony, and opportunities to meet Nature Center animal ambassadors.

A weekly 5K cross-country trail series at Worthington Winery in Somers, Connecticut, held Wednesdays from June 3 to July 1, 2026. The course runs through backwoods and vineyard areas with views of ponds and a covered bridge.