Long Island Vacation Ideas Long Island - Road Trip Planner
 

Most Scenic Drives in Long Island, Hamptons, Montauk, Fire Island

Things to do / Travel Guide

With its sweeping, sandy beaches, charming hamlets, rocky shoreline, majestic lighthouses, and centennial trees Long Island provides the driving tourist with breathtaking vistas. Nearly every stretch along Long Island's coastline is scenic, but here are a few specific drives that come highly recommended:

Scenic Drives around South Shore and the Hamptons, Long Island

Pick up Highway 27 in Hampton Bays and drive east, through the Hamptons' winsome Long Island hamlets, past sand dunes, until you spill out onto a thin strip of coastline that takes you through the lush Hither Hills State Park. The drive's grand finale is the elegant Montauk Lighthouse that stands, like a beacon, on a high, rocky promontory at the easternmost tip of Long Island. The drive is about 40 miles.

Running east from Westhampton to Hampton Bays and Shinnecock County Park West, Dune Road offers a superb view of the simple, modern, and eccentric Westhampton beach houses that line this thin strip of barrier beach. The drive is about ten miles.

Ocean State Parkway from Jones Beach State Park to Robert Moses State Park provides a beautiful coastline drive along Long Island's South Shore. On this narrow sliver of land you will pass through the lush Tobay Beach Park, Gilgo State Park, and Cedar Beach Golf Course - not to mention miles of refreshing ocean views. The drive is just over 15 miles.

Scenic Drives around Shelter Island, New York

For an equally beautiful scenic coastline cruise, pick up Shore Road in Dering Harbor on Shelter Island and wind your way along the shoreline of Shelter Island Sound. Shore Road ends on a small inlet of Shelter Island Sound, cross over the bridge and continue along Winthrop Road. This drive is less than ten miles. To get to and from Shelter Island board one of the convenient year-round ferries, North Ferry Company travels between the north side of Shelter Island and Greenport.
The ferry usually leaves every 20 minutes to a half an hour, and takes about seven minutes each way. Shelter Island South Ferry travels between the south side of Shelter Island and North Haven (near Sag Harbor), and takes about five minutes for a one-way trip. Ferries run from early in the morning until late in the evening.

Scenic Drives around North Shore, Long Island

For a scenic tour of the North Shore, pick up Route 25 near Southold and carry on this 36-mile National Scenic Byway to Orient Point. Lush trees canopy over the winding road that navigates through small, rural towns, bucolic wineries, and along beautiful shoreline stretches with tranquil blue expanses of sky and water.