Around the Fork: Orient Point to Montauk Point
Long Island’s East End splits into two peninsulas, the North Fork and the South Fork, separated by Peconic Bay. This route connects their outermost tips on foot, the long way around. You run east to west down the North Fork, around the head of the bay at Riverhead, then west to east out the South Fork to the end of the island.
Start at Orient Point, at the tip of the North Fork. Finish at the Montauk Point Lighthouse, at the tip of the South Fork.
Any line between the two points is acceptable as long as the whole distance is covered on foot and the route goes around the head of Peconic Bay at Riverhead. Road, trail, or any mix of the two. No ferries, boats, or water crossings. The North and South Ferries through Shelter Island are not allowed.
Expect somewhere between 78 and 82 miles depending on the line you pick, with about 1,850 feet of gain. There is no set path. Most road lines use NY-25 and County Road 48 down the North Fork, NY-24 through Flanders, and NY-27 out the South Fork, with local variations through the villages. On the South Fork the Paumanok Path runs most of the way from Southampton to Montauk Point and offers a trail alternative for anyone willing to trade pavement for terrain and navigation.
Road sections mean shoulder running on active highway. Resupply is good the whole way through the North Fork hamlets and the Hamptons villages. The one real gap is Amagansett across Napeague to Montauk, roughly ten miles with nothing open overnight. Summer traffic on NY-27 is heavy, so crossing the South Fork at night is safer and cooler. The last five miles into Montauk Point hold the steepest climbing on the route.
