2. Oyster Bay

Raynam Hall Museum in Oyster BayRaynam Hall in Oyster Bay

Oyster Bay, a hamlet in the Town of Oyster Bay, is a mix of old and new like much of the North Coast, with a rather modern downtown juxtaposed with historic homes and structures. Oyster Bay was settled by the Dutch in the early 1600s and by the English in 1653 under Peter Wright. The area soon became a Quaker community home to brothers John and Henry Townsend, and founder of Quakerism George Fox visited Oyster Bay near Mill Pond. Oyster Bay’s Raynham Hall served as British headquarters during the Revolutionary War, and Major John Andre often visited Lt. Col. John Graves Simcoe at the home. You may recognize the names Townsend, Andre and Simcoe from the AMC show TURN, about the first spy ring in America. Oyster Bay is perhaps best known today as the home of president Theodore Roosevelt, who lived at Sagamore Hill in present-day Cove Neck, a neighboring village. Typhoid Mary also worked for a wealthy family in Oyster Bay in 1906 before infecting six people with typhoid fever.

Sagamore HillSagamore Hill, home of Theodore Roosevelt

Roosevelt’s legacy reflects heavily throughout Oyster Bay, including Theodore Roosevelt Memorial Park which includes the Theodore Roosevelt Monument Assemblage, a collection of 24 stones and plaque that represent “chapters” and together form a “book” of Roosevelt’s life. A number of Roosevelt-related landmarks at places like Snouder’s Drug Store still remain. For both history buffs and those looking to learn more about Oyster Bay’s history, the village erected the Oyster Bay History Walk, a 1-mile loop that covers around 30 historic sites like Moore’s Building, the Oyster Bay Bank Building, the Waterfront Center, and the Octagon Hotel. Other significant historic sites include Christ Church (Roosevelt’s family church established in 1705), the US Post Office building, and the Ludlam Building. Oyster Bay is also home to a number of parks including Tiffany Creek Preserve and Beekman Beach. If Gilded Age mansions are your thing, another can be found at the Coe Mansion at Planting Fields.

In addition to its rich history, Oyster Bay also features a number of creative and ethnic eateries near the water, including Wild Honey, an American seafood restaurant. Popular American eateries range from 2 Spring to Coach Grill & Tavern, while Italian restaurants include Pietro’s Brick Oven Pizza and Autentico. Oyster Bay’s downtown also features some ethnic options like Home Sweet Home, which serves Chilean fare, Nikkei of Peru, offering Japanese-Peruvian fusion, and Lourdes Mexican Grill.