Begin at Long Beach, where you’ll find activities galore, including surfing lessons and a beach-side trapeze. Head to Jones Beach State Park and hit the pools and restaurants or catch a concert at Nikon, the beach’s amphitheater. Grab your fishing pole and set off on a charter from Captree State Park. Don’t miss 50-kilometer-long Fire Island, accessible only by ferry. Venture out on a hike through the 300-year-old Sunken Forest located just behind the beach dunes. Long a haven for the LGBT community, Fire Island’s festive village Cherry Grove is the place to be.
Some of the USA’s finest thinkers and artists lived and worked on Long Island. Tour painter Jackson Pollock’s house and studio at the Pollock-Krasner House and Study Center and see the floor of the studio (once a barn) covered in paint. Walk through the home of America’s first “Poet of Democracy” at the Walt Whitman Birthplace State Historic Site, then visit the “Summer Whitehouse” of President Theodore Roosevelt who kept his residence at Sagamore Hill throughout his presidency. Or, follow the Washington Spy Trail, which tells the story of a group of citizens who risked their lives to get George Washington the information he needed to win the American Revolutionary War.
Rent a bike and visit some of the 30-plus wineries in Long Island Wine Country (or sign up for a vineyard tour). Along the way, you’ll find organic farm stands, you-pick farms for apples and pumpkins, and farm-to-table restaurants taking advantage of the region’s rich soil and temperate growing conditions. Meander among seaside villages rich with maritime culture and along rural roads that wind through acres of farmland and vineyards. Time your visit to coincide with festivals and fairs celebrating wine, craft beer, harvests and seafood.
No visit to Long Island is complete without taking a Gold Coast Mansions Tour, launching right into the Gilded Age of “The Great Gatsby,” which was inspired by the immense estates here. Old Westbury Gardens and Oheka Castle are open to the public, but you’ll see others from the road. Take a further step back in time at Stony Brook Village and learn about the area’s role in the Revolutionary War and the Washington Spy Trail. Visit Old Bethpage Village Restoration, a recreated mid-19th century village, to see what life was like here before the Roaring Twenties.
