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 on the far side or the Montauk Point Lighthouse on the rocks closest to the water, 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 easy on the North Fork and through the Hamptons villages, though a few stops through Southampton sit a short detour off the main line. 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.
What makes it special
For most of the day you can see where you are going and it does you no good. Peconic Bay is only a few miles wide, so you run west down the North Fork looking across at the South Fork, which you will not reach for another forty miles. Everyone out here crosses that water by ferry. This route refuses the shortcut, and that is the whole idea.
You get the entire East End in one push. Farm fields and vineyards, the head of the bay at Riverhead, the Hamptons villages after dark, open dunes at Napeague in the middle of the night, then the last hills into Montauk Point, the easternmost land in New York State.
The two forks are the tail end of the same ridge of hills, split by the bay. Running around them covers both sides and everything between.
