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To give you the most unique and exciting travel experiences, the Utrip team curates each destination with a combination of human expertise and artificial intelligence. We’ve done the heavy lifting and sorted through thousands of activities, restaurants, and nightlife so that you don’t have to. Our Refined & Enhanced destinations include original content and local recommendations, providing a special touch so that you can plan your perfect trip. Learn more about the Utrip process.

Overview

Long Island is a quintessential American cultural and historical powerhouse. Western habitation of the island began in the early 1600’s with the arrival of European settlers from nearby Connecticut. As time progressed, Long Island played a critical role in the American Revolution, gave birth to Walt Whitman, and saw the precipitous rise of the monetary elite generated by the Industrial Revolution - a time known as the Gilded Age. When we look at the 20th century, the island has given birth to such names as Billy Joel, a music superstar, and Julius Irving, a legendary basketball player who earned the nickname Dr. J. Can’t forget to mention Charles Lindbergh, of course, whose transatlantic flight established the island as an aviation center. Beyond the historic sites, it’s also an understated tourist mecca with activities ranging from stunning white-sand beaches, to sprawling nature preserves, and vineyards galore. It’s hard to imagine how this place isn’t jam-packed with tourists from Queens in the east to Montauk Point at its western terminus. 

Long Island’s historical resources are practically innumerable when speaking in terms of travel — there’s no possible way to fit them all into one trip. You could start at the beginning with the simply named “Old House” in Cutchogue, originally constructed in 1649 when the Montauk and Shinnecock Natives still inhabited the land. Or you could start with the unrivaled glitz, glamor, and luxury portrayed by the Great Gatsby-era dames with appropriately epic monikers such as Old Westbury Gardens, Oheka Castle, and Castle Gould. They were built by the industrial leaders, the celebrities of their day, in the late 19th and early 20th century. The houses shined for only a few years before the 16th Amendment passed in 1913, which instantiated federal income tax and brought that era of palatial mansions to an end. The legacy of wealth, however, carried over to today’s celebrities and financial leaders who now build their own statements of success in the Hamptons and along the Gold Coast. Alternatively, you can take a look through political history by seeing Sagtikos Manor, which originally served as an outpost for the British military before the revolution, and played host to George Washington post-conflict. Sagamore National Historic Site contains the summer White House frequented by Teddy Roosevelt during his presidency, and the William Floyd Estate is the ancestral home of William Floyd himself, a signer of the Declaration of Independence. 

It’s easy to assume that Long Island’s culinary history is rather fishy and unremarkable. Even that, however, is untrue. The battle for chowder supremacy rages on forever between the Northeastern states — should it be red? How about clear? Maybe that creamy stuff from New England? Grab a bowl with some oyster crackers and decide for yourself, a perfectly hearty meal to precede wine tastings at one of the 38 vineyards that dot the island. The award-winners include Martha Clara, Bedell Cellars, and Sparkling Pointe. Play it safe, and take a bike tour between them. Although, by the end, you might be walking those wheels, giddy with the memories of palate placating Pinot pairings. 

As for the rest, there’s almost too much to cover. Walt Whitman, the iconic Transcendalist leader, was born and raised here and his childhood home is now a museum open to the public. Jackson Pollock, the undisputed leader of the Abstract Expressionist movement, moved to the island after he married a fellow artist and required a space for both of them to create and live — a place you can visit to marvel at some of his creations. The Cradle of Aviation hosts permanent exhibits detailing the importance of the aerospace industry to the island’s economy. It’s possible to visit and learn about an endangered ecosystem, the Maritime Holly Forest, on Fire Island where the perfect balance of preservation and access allow people to learn without damaging the ancient plants. And then there’s the beaches, countless beaches, all with white sand and rolling waves whose burbling invitation calls people out from New York City and Upstate to escape the urban and inland heat waves. 

Grab a glass of wine, a history book, some good walking shoes, and sunblock because you’re gonna need them all when you inevitably fall in love with an island that is as American as apple pie. 

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North Fork Roasting Company

Artisanal Goodness

Nassau County Museum of Art

Nassau County Museum of Art

Bruce and Son

All-Day Brunch Spot

Belmont Lake State Park

Belmont Lake State Park

Fire Island National Seashore

Fire Island National Seashore

Montauk Point Lighthouse Museum

Montauk Point Lighthouse Museum

Oyster Festival

Oyster Festival

1943 Pizza Bar

Celebrating Pizza

Brand's Delicatessen

Fast and Friendly

Adventureland

Adventureland
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