Oyster Bay

Theodore Roosevelt spent his summers on a hill above the bay, and from here he ran the country as president during his vacations – Sagamore Hill became the “Summer White House.” A trip to Oyster Bay takes you to the North Shore of Long Island, where the Gold Coast mansions evoke the world of Gatsby, all the way to the Atlantic beach communities in the south.

A Town from Coast to Coast

Oyster Bay is a town in Nassau County that stretches like a narrow ribbon across Long Island – from Long Island Sound in the north to South Oyster Bay. It includes the hamlet of Oyster Bay, from which it takes its name, as well as places such as Syosset, Bethpage, Massapequa, Hicksville, and Jericho. The Dutch and the English fought over the area in the 17th century, and during the Revolutionary War, spies of the Culper Ring operated here. Around 1900, industrialists such as the Vanderbilts, Morgans, and Coes built magnificent country estates along the North Shore, which are said to have inspired F. Scott Fitzgerald's “The Great Gatsby.”

Sights in Oyster Bay

Sagamore Hill National Historic Site preserves Roosevelt's home, with its hunting trophies, books, and furniture in their original condition; his grave is located nearby at Youngs Memorial Cemetery. Planting Fields Arboretum State Historic Park, with the Tudor Revival mansion Coe Hall and its greenhouses, is among the most beautiful gardens in the region. In the hamlet of Oyster Bay, the Raynham Hall Museum showcases a house from the colonial era, and in summer the historic oyster sloop Christeen sails from the harbor. In the south of the town lies Bethpage State Park with its famous Black Course, which has hosted several U.S. Opens and, in 2025, the Ryder Cup. Tobay Beach on the south shore offers an Atlantic beach.

Eating and Going Out in Oyster Bay

As the name suggests, oysters from the bay are part of the tradition, and in October the town celebrates the Oyster Festival with food stands, music, and oyster-shucking contests. Seafood restaurants serve clam chowder, lobster rolls, and grilled fish. A large Indian community has settled in Hicksville, with restaurants and shops along the Broadway corridor. Pizzerias and Italian delis are, of course, part of everyday life on Long Island anyway. The nightlife is rather quiet; people meet up in pubs or head into Manhattan.

Touring the Gold Coast Mansions

Some of the Gold Coast estates are open to visitors. In addition to Coe Hall at Planting Fields, these include Oheka Castle in neighboring Huntington, a Loire-style château that is now a hotel and event venue. Sagamore Hill offers tours of the restored family home, and the nearby Theodore Roosevelt Sanctuary commemorates the president as a conservationist. If you have more time, drive along the winding roads of the North Shore, past gates and tree-lined drives, behind which more estates lie hidden.

Getting Around Oyster Bay and the Best Time to Visit

Several Long Island Rail Road lines connect the town's communities with Penn Station and Grand Central in Manhattan; the trip to Oyster Bay station takes about an hour and a half. LaGuardia and JFK airports are roughly 40 to 60 minutes away. A car is handy for the Gold Coast mansions and parks. The best time to visit is from May to October, when the gardens and beaches beckon; fall, with its colorful foliage and the Oyster Festival, is especially appealing.