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Although two of New York City's boroughs, Brooklyn and Queens, occupy the island's western section, the real Long Island begins only when you leave the city behind and cross into Nassau County. East of Nassau is the more rural Suffolk County, with its North and South forks extending far into the Atlantic Ocean. The north-south distinction also applies to the North and South shores that run the length of the island.
There's plenty to see on the island, but you'll spot nothing but traffic from the Long Island Expressway (U.S. 495, known to most residents as the LIE), which runs through the middle of the island from Long Island City in Queens all the way east to Riverhead in Suffolk. Summer weekends can be particularly problematic, when people head straight for either the South Shore's Fire Island or the South Fork's Hamptons and points east to Montauk. If you're more interested in the museums, stately mansions, nature preserves, and other attractions of the North and South shores, take the more leisurely roads that follow the two coastlines. On the North Shore, your best bet is Route 25A; on the South Shore, follow Route 27 (Sunrise Highway). Many north-south roads connect the shores, so cutting back and forth is easy. If your schedule is tight, stick to the LIE or the Northern State or Southern State parkways to make the best time between points of interest.
By choosing the most direct route, it's possible to drive from Manhattan to Montauk Point in less than three hours—although rush-hour and weekend traffic can cause significant delays. Once you reach Riverhead on the LIE, Long Island separates into the North and South forks. Each fork is traversed by a two-lane highway (Route 25 on the North Fork, Route 27 on the South Fork), and the surroundings become increasingly rural the farther east you go. Be prepared for travel to slow considerably once you are on the forks, especially in the height of summer; there are, however, lots of interesting farm stands and shops along the way to take your mind off the slowdown. Shelter Island, between the two forks, is a destination in itself; the only way to get here is by a short ferry ride from either Sag Harbor, on the South Fork, or Greenport, on the North Fork.
Noteworthy attractions of the North Shore, which stretches from Great Neck to Port Jefferson, include Teddy Roosevelt's summer home at Sagamore Hill, Walt Whitman's birthplace at Huntington Station, and Gold Coast mansions. North Fork highlights include quiet villages, bountiful farm stands, and the vineyards and tasting rooms of a burgeoning wine industry. The cultured yet buzzing Hamptons, the fascinating old whaling village of Sag Harbor, and majestic Montauk Point are the essence of the South Fork.