Long Island Loop
United States
Beginning and ending in New York City, this Long Island circuit heads east on the Expressway to Montauk, then returns down the Southern State past 30 vineyards, Hamptons mega-mansions, unspoilt North Fork farmland, Shelter Island, and Fire Island (car-free, visit on foot). Allow four days for the Gilded Age beach resorts, Cedar Point lighthouse, and the Sagamore Hill home of Theodore Roosevelt.
Explore on the interactive map →Stops along the route
- Central Park
The loop departs east via the Queensboro Bridge onto I-495. Within 30 minutes the Manhattan skyline dissolves into Long Island's North Shore Gold Coast.
- Montauk Point Lighthouse
New York's oldest lighthouse, built 1796, stands above seal-inhabited rocks at Long Island's eastern tip. The surf town below has resisted full Hamptons gentrification.
- East Hampton
The social capital of the Hamptons, lined with cedar-shingled mansions and galleries. The Pollock-Krasner House in Springs preserves the studio where drip painting was born.
- Sag Harbor
A former whaling port with a perfectly preserved 19th-century Main Street. The Whaling Museum occupies an 1845 Greek Revival mansion built from a single whale-oil fortune.
- Shelter Island
Reached by ferry from North Haven, a third of this quiet island is the Mashomack Nature Preserve of tidal creeks, osprey nests, and white-tailed deer.
- North Fork Wine Country
Thirty vineyards along a 24 km corridor produce Long Island's best Merlot and Cabernet Franc. Bedell Cellars and Pellegrini Vineyards are the flagships.
- Fire Island National Seashore
A car-free barrier island reached by ferry from Bay Shore. Boardwalk communities, a 19th-century lighthouse, and 50 km of undeveloped Atlantic beach.
- Jones Beach State Park
Robert Moses's 1929 masterpiece stretches 10 km along the Atlantic with its Art Deco water tower landmark. The Southern State Parkway feeds directly into the park's grand entrance.
- Coney Island
The democratic beach at journey's end. The 1927 Cyclone, Wonder Wheel, and Nathan's Famous hot dogs close the loop 90 minutes by subway from where it began.
Where to Eat
- The Lobster RollSeafood
A classic roadside eatery in Amagansett, famous for its lobster rolls and casual beachside atmosphere.
- Nick & Toni'sItalian
Upscale Italian dining in East Hampton, known for its wood-fired pizzas and celebrity clientele.
- Claudio's RestaurantSeafood
Historic waterfront restaurant in Greenport offering fresh seafood and harbor views.
- Peter Luger Steak HouseSteakhouse
Iconic Brooklyn steakhouse renowned for its dry-aged steaks and old-school charm.
Things to Do
- Montauk Point State ParkNature
Explore scenic trails and enjoy panoramic ocean views at the eastern tip of Long Island.
- Parrish Art MuseumMuseum
Contemporary art museum in Water Mill showcasing works by American artists with a focus on the East End.
- Long Island AquariumAquarium
Family-friendly aquarium in Riverhead featuring marine life exhibits and interactive experiences.
- Luna ParkAmusement Park
Historic amusement park in Coney Island offering classic rides and carnival games.