Robber baron Jay Gould built both mansions for his wife, who was later accused of having an affair with Buffalo Bill (yes, that Buffalo Bill). Don't miss the Sands Point Preserve, which features the famed Hempstead House. The estate is now a museum with stellar landscaping. Henry Phipps was Carnegie's business partner, and the trust he created for his family has made them modern-day billionaires.

Start with Old Westbury Gardens of the Phipps fortune. There are so many Jazz Age estates on Long Island that you can tour them along what is dubbed the Gold Coast of Long Island. Just keep in mind that many hotels and restaurants on Shelter Island only welcome visitors seasonally. A local favorite is the Shipwreck Bar at the SALT Waterfront Bar & Grill. Sunset Beach hotel is another fantastic Shore Road hotspot, with 'froze' (frozen rose) on tap. Try The Pridwin Hotel their restaurant looks out over a grand lawn. There are chockablock charming bistros, but the real dining scene is at the island's hotels. No trip to Shelter Island is complete without an alfresco meal. Shelter Island is all about getting outside, whether it's biking around town (cars require a permit to park) hiking Mashomack Preserve, which covers one-third of the island golfing at the Shelter Island Country Club or simply sunning at one of its many beaches, such as Wades, Crescent or Sunset. The admirers of Shelter Island prefer its more low-key vibe to the posh Hamptons, though there are still plenty of yachts. Shelter Island is a short ferry ride from Sag Harbor and a secluded summer refuge.

For something a bit less eerie, head to Deep Hollow Ranch, where beginners and experienced riders can enjoy the horses at the self-proclaimed oldest working ranch in the United States.

Hikers will eventually come across the abandoned Cold War-era radar tower that was once part of Camp Hero, a spooky destination that evokes conspiracy theories. We recommend a drive down Montauk Highway or a hike at Camp Hero State Park, where the vista along its cliffs feels a bit like a baby Big Sur. It's not the only place for views, though – far from it. The Montauk Point Light is also a must, though it gets crowded during the middle of the day. Tourism in the Hamptons hasn't slowed since, but much of Montauk remains the same. Immortalized in song by The Rolling Stones in the '70s, Memory Motel still stands and welcomes revelers along the Montauk Highway. The city attracts loyal summer crowds for its stunning beaches and family-friendly downtown. An old fishing village at the very end of Long Island, Montauk is the easternmost point in New York.

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