Trail Running calendar near East Hampton 2026-2027

Hit the trails at Pittsfield State Park for the Tails & Trails State Forest Run. Choose from 50K, 25K, or 5-mile distances on a scenic loop course. The event supports 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.

Two trail races, a new half marathon and a 6k sampler, weave through the scenic Shenipsit State Forest past the Soapstone Mountain tower. The event supports local trail stewardship. A cupless race, it's organized by the nonprofit Shenipsit..

Run a 3.5-mile trail race in Wolcott, CT. The event supports the local cross country teams. Your entry includes access to the CT Food Truck Battles Festival afterward.

Join this adventure based event in Barrington featuring a 1.5 mile neighborhood loop and an accessible adaptive course. This family focused run includes electronic timing and performance shirts for the first 1,000 participants.

Experience Long Island trail running with a full marathon or 15 mile race at Bethpage State Park. Support the local Greenbelt Trail Conference while exploring the natural paths of Farmingdale.

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.

Experience a scenic road race past historic farms and through the Litchfield Hills starting at the Mine Hill Distillery. This half marathon features a challenging uphill first half followed by a fast downhill finish.

Experience a scenic trail race through the historic Powisset Farm and Noanet Woodlands. Choose from four distances featuring grassy farm paths and forested trails including a climb up Noanet Peak.

Operation Mohawk Tactical 2 unites the Mohawks Medevac and Honor & Remember 5 Miler events. It takes place at F Gilbert State Forest in Foxboro, supporting veteran and first responder suicide prevention. Participants can run, ruck, walk, or..

ENDURE is a Last Man Standing running event where participants complete a fixed loop every hour. The last runner standing wins, with a central hub for recovery and community. It's designed for all levels, from seasoned endurance athletes to..

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.

Experience a timed 5K trail race through the scenic meadows and woods of Coogan Farm in Mystic. Enjoy post race festivities with animal ambassadors and support local environmental conservation at this inaugural event.

Test your limits at this multi day vertical endurance series at Mohawk Mountain. Choose from seven elevation based challenges ranging from 12 to 84 hours as an individual or part of a flexible relay team.

Overview The Connecticut Ultra Traverse (CUT) is a point-to-point trail running event with two distances. The CUT112 is a 112 mile run following the Blue Blazes of the New England Trail (NET) from the Massachusetts-Connecticut border to the..

Experience a timed 5K trail run or walk through the scenic woods and fields of the Van Vleck Farm and Nature Sanctuary. Enjoy live music and food trucks at this annual community event in Woodbury.

The Rockwood Ramble 10K offers a scenic run on carriage roads through the woods of Rockefeller State Park Preserve. The event features a standard 10K and a separate kids' run, with all proceeds supporting trail maintenance.

Run a flat, out-and-back course on the scenic Holliston Rail Trail. This event offers a 5K and a 10K for adults, plus a fun run for kids with distances based on age. The community gathering point is Blair Square in Holliston.

The Levee Loop Trail Race 10K - Islip will take place in Islip on Saturday 6 June 2026. You can run between 5 and 10 kilometers.