The best road on Long Island isn’t the expressway, and it isn’t even Montauk Highway itself. It’s the old road at the very end of the South Fork: Old Montauk Highway. That’s what Montauk Highway used to be, the only road out to Montauk, until the parkway got run through. Now it’s a narrow road along the shore, big ups and downs, tight curves.
It’s the best because once you get past the Shinnecock Canal the strip malls go away and you start seeing farmstands. Then you’re breathing that heavier ocean air. Then you forget where you’re supposed to be in an hour because you start wanting to stop somewhere. You do this because you’re driving an old road like this to wander, not to get anywhere fast.
Old Montauk Highway only became the old road in 1930, when Robert Moses and the state parks commission decided to carve a brand new parkway through the woods farther north. The old one had done fine for about fifty years. Moses said that the six miles between Fort Pond and Third House had to follow the old road because the land along it had already been sold.
As of 2005, from Hither Hills to Fort Pond, and from the intersection near Third House to Camp Hero, you can follow the old highway by car. The stretch to the Point at Montauk used to be open to cars, but it’s been closed for a long time.
The speed limit seems to be set at 30 most places, but that’s not what you’ll end up doing, not on a hilly, curvy road like that. In November 2024 the town eyed cutting its roads to 25 but left this one out of the first round.
Just Take Montauk Highway
Getting to Old Montauk Highway is easy: just take Montauk Highway. Past the Shinnecock Canal it’ll cut straight east through Southampton, a formal and historic old town. If you want to ogle the life of the rich for a little while, take the detour onto Gin Lane south of Southampton’s Main Street. Privet hedges as high as fifteen feet keep the estates hidden, but you’ll catch glimpses of the Atlantic between them.
Past Bridgehampton village and Main Street and farm markets where fresh produce outsells imported specialty goods, it’s on to East Hampton, past the windmill on the village green and the little commercial strip where galleries outnumber gas stations. A few minutes more and you’re at Main Beach, with its lifeguards.
Depending on the season, a beach stop here can be easy or difficult. Cooper’s Beach in Southampton has white sand and big dunes that routinely rank it among the top beaches in the country. Main Beach also has restrooms and outdoor showers. On summer weekends parking fills early, but early weekday mornings are fine.
If you need coffee and pastries when you arrive in Amagansett, Jack’s Stir Brew or Amber Waves Farm are worth pulling off the road for. Amber Waves is more interesting: a nonprofit teaching farm with a market cafe. After that it’s a straight road beside the ocean. The ocean’s to the south, beach grass and old weathered fences on both sides. Late in the season roadside farmstands have produce and beautiful flowers.
When you leave Amagansett for Montauk the highway narrows. The trees press in close on both sides, and for a minute you’d swear you were driving the coast of Maine. Then it’s the old road, going through Hither Hills.
The State Park
Hither Hills State Park is open every day of the year from sunrise to sunset. If you arrived by car, it charged $10 per vehicle from May 23 to September 13, 2026, 8 a.m. to 4 p.m.
The Montauk Point Lighthouse is New York’s oldest, commissioned by George Washington in 1792. The state park around it has trails, cliff views, and if you’ve got time, budget an hour for the whole thing. If you’re visiting from October 17 to November 11 you only need to pay a fee on weekends and holidays this year.
Ditch Plains draws surfers from far and near, but stop even if you don’t surf, for the atmosphere. The parking lot sits high enough that you can usually get a good view, and if you walk in either direction you can usually find a quiet spot where the crowd isn’t.
Three stops are worth detouring for:
- Bagatelle in Montauk for waterfront seafood, and views of the working fishing fleet;
- Sag Harbor Whaling and Historical Museum, off Route 114; and
- Cedar Point County Park, with trails down to the water and a lighthouse.
Fill your tank and a cooler in Southampton. In Montauk gas stations start getting scarce, and the prices climb. Route 27 clogs up westbound on Sunday afternoons in peak season. Weekdays you’ll usually find an open road.
The weather turns fast out here. Morning fog usually burns off by midday. Early fog can cut visibility badly. Wind can sometimes get strong enough to change how the car handles. Rain turns the detours to the beach into mud. Check the forecast before you leave and plan on being flexible.
The best of it, you’ll find, happens between planned stops: a farmstand you never looked up, a beach the locals use, a back road where estates give way to woods. Now and then it makes sense to leave extra buffer time, so you don’t feel compelled to hurry, because you never know what you’ll discover if you just get out and walk.
