Tavern Island in Norwalk, CT: A Historic Hideaway with a Party Past

Most private islands offer solitude. This one offers history, intrigue, and a long list of legendary visitors. Tavern Island (pics), a three-and-a-half-acre retreat off the coast of Norwalk, Connecticut, has seen everything from Revolutionary War battles to celebrity-filled parties.

First inhabited by European settlers in 1651, Tavern Island played a strategic role in the American Revolution. During the Battle of Norwalk in 1779, it served as a lookout point, guarding the entrance to Rowayton Harbor against British forces. More than two centuries later, while dredging near the island, workers pulled up an old cannon—an artifact likely dating back to that time. The island is said to have earned its name from early ship captains who used it as a drinking spot after docking.

By the early 20th century, Tavern Island had shifted from military significance to a private retreat. The island’s main house, a 6,116-square-foot English country-style manor, was built in 1900. The residence has six bedrooms, four full bathrooms, and three half-bathrooms.

In addition to the main house, the island includes a caretaker’s cottage dating back to the Civil War era, a Japanese-style tea house with a bedroom and meeting room, and a boathouse with a game room and guest accommodations. A private dock provides access to the mainland in just five minutes.

The island features two private beaches, a deep-water dock, and a 75-foot, competition-length swimming pool suspended over the water’s edge. When last sold, the property included a docking area and garage on the mainland, plus two boats for quick transportation.

Tavern Island’s most famous owner was Broadway showman Billy Rose, known for his extravagant parties. He hosted Hollywood icons like Marilyn Monroe and Barbra Streisand, turning the island into a social hotspot. One local recalls that as a teenager, she and her friends would try sneaking onto the island—only to be shooed away when the parties got too wild.