Pirates Invade Sheffield Island: A Swashbuckling Summer Adventure Awaits July 18 & 19

Yo, ho, ho—and a barrel of fun is headed for Sheffield Island Lighthouse when the annual Pirates Weekend & Cruise sets sail on July 18 and 19, 2026. Hosted by the Norwalk Seaport Association, this wildly popular event turns a scenic island getaway into a full-on high-seas escapade for the whole family, complete with treasure hunts, sea chanteys, and enough swashbuckling spirit to make your inner captain shout, “Ahoy!”

The adventure begins at 90 Water Street in South Norwalk, where guests board the ferry and cruise across the sparkling waters of Norwalk Harbor. Along the way, you’ll pass charming islands, historic lighthouses, and sweeping coastal views—basically, a scenic prelude to your pirate destiny. Ferries depart at 10:00 a.m., 11:30 a.m., and 1:00 p.m. So arrive early—these boats wait for no matey! Secure your spot with Pirates Weekend Ferry Tickets at seaport.org/events and set sail before the crew swabs the deck without you!

A Pirate’s Playground 

Once ashore, Sheffield Island turns delightfully rogue. The day comes alive with the legendary Bawdy Buccaneers—a professional troupe of pirate re-enactors who bring history to life with just the right amount of mischief. Between treasure hunts on the private beach, interactive pirate games, sea chanteys, storytelling, and dramatic swordplay, there’s no shortage of high-seas hijinks. Add in tall tales of danger, mystery, and the open sea, and you’ve got yourself a day fit for the fiercest pirate and mistress of the high seas.

Best of all, every bit of this eyebrow-raising adventure is included with your ferry ticket, which is a pretty sweet deal for a day this delightfully unruly. And while the pirates are having their fun, the island still has plenty to teach: Pirates Weekend is also a chance to step into maritime history. With the historic lighthouse standing watch, guests of all ages can explore the legacy of seafarers and pirates, the importance of preserving Long Island Sound, and the stories behind one of Connecticut’s most iconic lighthouses. In short: it’s part history lesson, part pirate party, and entirely unforgettable.

About the Norwalk Seaport Association Founded in 1978, the Norwalk Seaport Association is dedicated to preserving and celebrating the region’s rich maritime heritage. Through educational programs, lighthouse tours, and unforgettable on-the-water experiences, the organization connects visitors of all ages to the history, environment, and beauty of the Norwalk Islands. Their mission is simple yet powerful: to strengthen the connection between past, present, and future through preservation, education, and community engagement.