Top 10 Most Awesome Reasons to Visit New York's Long Island

The Must-Sees: Vineyards, Beaches, the Hamptons and Historic Sites

Montauk Point
••• The lighthouse at Montauk. Michael Orso/Getty Images

At 118 miles long, Long Island has bragging rights as the longest island in the contiguous United States. Even though it's close to famed New York City, Long Island can hold its own when it comes to attractions. With sugar-fine beaches, the glamorous Hamptons, famed golf courses and much more, Long Island has much to offer. Here are the top 10 reasons why you should visit Long Island.

For family-friendly fun, please see: Top 10 Children's Attractions on Long Island.

  • 01 of 10
    Man on East Hampton beach at sunset
    ••• Mitchell Funk/Photographer's Choice/Getty Images

    Stephen Leatherman, aka "Dr. Beach," consistently picks several Long Island beaches for his annual list of America's Top 10 Beaches. It comes as no surprise. From Long Beach's three mile-plus stretches of powder-fine sands to the pounding surf of Montauk and the celebrity haunts in the Hamptons, Long Island without a doubt features some of the world's most spectacular beaches.

  • 02 of 10
    Row In Vineyard, Sag Harbor, New York, Usa
    ••• Keith Levit/Getty Images

    Benefiting from a microclimate similar to that of Bordeaux, France, Long Island's East End features one great vineyard after another. Most are on the North Fork, but you can find a few on the South Fork as well. Remember that the delicious wines don't necessarily have to be expensive. Read about affordable Long Island wines and see for yourself.

    Most Long Island vineyards hold free wine tastings with entertainment on the side. Many of the vineyards are available for Wine Country weddings, set against the backdrop of beautiful acres of picturesque grape vines.

  • 03 of 10
    41st Annual Hampton Classic Horse Show
    ••• The Hampton Classic Horse Show. Sonia Moskowitz/Getty Images

    One of the most famous areas on Long Island, the Hamptons are renowned as home to the rich and famous. Located on the South Fork on the easternmost end of Long Island, the area encompasses the towns of Southampton and East Hampton, with their many hamlets and villages, including Sag Harbor, Water Mill and Bridgehampton, home to the annual Hampton Classic horse show. With miles of stunning beaches, museums, fine dining and celebrity watching, the Hamptons attract an annual summer crowd from other parts of Long Island, the greater New York City area and beyond.

  • 04 of 10
    Montauk Point
    ••• Michael Orso/Getty Images

    Although technically a hamlet within the town of East Hampton, Montauk is often billed as the "un-Hamptons" with its laid-back pace and surfer culture. Montauk boasts some of the most gorgeous sand and surf on the island. In 2009, "Surfer" magazine named it one of the 10 Best Surf Towns in America. Montauk's legendary Gurney's Inn has welcomed visitors from Long Island and elsewhere since 1926 and features its elegant Sea Water Spa and more. The resort provides a breathtaking beachfront backdrop for weddings and receptions. The historic Montauk Lighthouse, which was commissioned by George Washington, is open to the public. There's golf, spectacular state parks, great restaurants and much more to explore in Montauk.

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  • 05 of 10

    There are several private and public golf courses situated on Long Island's gently rolling landscapes. Bethpage State Park features five world-class, 18-hole courses, but the most famous one is its Black Course. In 2002 and 2009, the challenging Black Course was the backdrop for the U.S. Open. If you're not on a par with Tiger Woods or Lucas Glover, you can always play the Green, Red, Yellow or Blue courses here. Bethpage State Park is located at 99 Quaker Meeting House Road, Farmingdale. 

  • 06 of 10
    USA, New York, Long Island, Oyster Bay, Sagamore Hill, Historic home of former US president Theodore Roosevelt
    ••• Walter Bibikow/Getty Images

    Once known as the "Summer White House," the former estate of the nation's 26th president, Theodore Roosevelt, is now a national historic site in Oyster Bay. You can take a guided tour of the impressive 23-room home and see where the former president lived and entertained heads of state. On the grounds, you can also enjoy the Roosevelt museum and nature trails on the grounds that he and his family once enjoyed. Each Fourth of July, there's a free celebration that includes a visit from "Teddy Roosevelt," an actor who bears an uncanny resemblance to the late president.

    Sagamore Hill National Historic Site, part of the US National Park Service, is located at 20 Sagamore Hill Road, Oyster Bay. 

  • 07 of 10
    Nassau County Art Museum
    ••• Pamela V. White/Flickr/CC BY 2.0

    In 1919, industrialist and patron of the arts Henry Clay Frick gave his son, Childs Frick, and his bride, Frances, a present that few today could afford: a Georgian mansion, surrounded by 200 verdant acres. The mansion, once known as "Clayton," and its surrounding property is now the home of the Nassau County Museum of Art with a permanent art collection by luminaries including Edouard Vuillard, Pierre Bonnard, Roy Lichtenstein, Auguste Rodin, Georges Braque and others. The grounds contain an Outdoor Sculpture Garden with works by renowned artists such as Niki de Saint Phalle, Fernando Botero and Tom Otterness.

  • 08 of 10
    South Ferry at Shelter Island
    ••• Roger Ressmeyer/Corbis/VCG/Getty Images

    Located between Long Island's North and South Forks, Shelter Island is a short ferry ride from either tip of the Island. Walk along the beach, rent a bike or boat and explore the New England–like feel of this laid-back island. Spend a long weekend exploring Shelter Island on your own, or take a guided walk through Mashomack Nature Preserve, 2,000 acres of unspoiled greenery owned by the Nature Conservancy.

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  • 09 of 10
    Early 20th century stairway entrance to a large estate that has been turned into a hotel.
    ••• Elliott Kaufman/Getty Images

    Does the opening scene of the Orson Welles classic, Citizen Kane, look familiar? If so, you might have been to Oheka castle, the former estate of wealthy financier Otto Herman Kahn. Built in 1919 to resemble a French château, the castle was the scene of soirees where the likes of legendary opera singer Enrico Caruso entertained guests. The lush gardens were designed by Frederick Law Olmsted, designer of New York City's Central Park. The Gatsby-era estate has been restored as a hotel and remains as the backdrop to sumptuous Long Island weddings. Also available at Oheka: a beautiful golf course and tennis courts. The castle is located at 135 West Gate Drive in Huntington. 

  • 10 of 10
    Flowers and garden path
    ••• Enn Li Photography/Getty Images

    The former estate of financier John S. Phipps, the mansion and 200-acre expanse of Old Westbury Gardens are listed on the National Register of Historic Places. You can take a tour of the sumptuous mansion with its rich wooden panels and fireplaces, decorated ceilings and artwork. The formal gardens include statuary like the pair of 18th-century French sphinxes that seem to stand guard over the entrance to the sprawling greenery. Old Westbury Gardens is located at 71 Old Westbury Road in Old Westbury.