Most parts of Long Island that are close to New York City are stuffed with charmless strip malls, chain restaurants and traffic-jammed local roads. Hit the highway and travel to Long Island's far, far east, and you'll encounter a landscape of winding country roads, farm stands and an expanse of wineries that remind visitors of California's Napa Valley.
Out in Montauk, New York on the South Shore, there's even a dude ranch. Yes, on Long Island you can find a taste of the west on the east coast. Few people realize that Long Island has a forgotten ranching history that goes back 350 years. The Island is even called the “birthplace of the American cowboy” by the Deep Hollow Ranch in Montauk, the oldest working ranch in the United States.
Visitors can learn to ride on Long Island beaches, rolling pastures and well-worn Native-American trails. Kids can also discover Indian culture by interacting with local Native-Americans when attending Deep Hollow's summer day camp.
New York State has a growing reputation for wine production that rivals California's. Long Island is the southernmost and the warmest part of the state with a climate similar to Southern France. The east end of Long Island is particularly friendly to vintners, as it's regarded as the best climate for raising grapes.
The first winery on Long Island was established in 1973; New York State is currently the third largest wine-growing region in the United States with over 300 wineries that generate over $4.8B.
Over a million people each year visit the 50+ wineries on Long Island. Long Island's east end is accessible by car or by train. The Long Island Rail Road organizes day trips from Manhattan to the best sights on Long Island.