Pirates Invade Sheffield Island A Swashbuckling Summer Adventure Awaits -July 18 & 19, 2026

 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 the mistress of the high seas. 

Best of all, every bit of this eyebrow-raising adventure is included with your ferry ticket. 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. Guests are invited to tour the lighthouse, uncover the legacy of Sheffield Island’s light keepers, and learn why preserving Long Island Sound matters. This popular event is 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.

Docktails & Oysters A Seaside Celebration of Flavor & Tradition Hosted by the Norwalk Seaport Association June 20, 2026

 Mark your calendars for Saturday, June 20, 2026, and prepare for an unforgettable evening on the water. From 5:00 p.m. to 7:00 p.m., the Norwalk Seaport Association, in partnership with fourth-generation oyster farmers Norm Bloom and Son, invites you to its signature summer celebration — Docktails and Oysters. Set against the stunning waterfront backdrop of the historic Norm Bloom and Son dock in Norwalk, this one-of-a-kind event blends fresh-from-the-Sound oysters, live music, local flavors, and maritime tradition into a celebration like no other.

 

Beyond the food and festivities, Docktails & Oysters supports a meaningful cause. Every ticket purchased benefits the Norwalk Seaport Association’s educational programming and the ongoing restoration and maintenance of Sheffield Island Lighthouse. “For guests who have sailed to the lighthouse aboard one of the Association’s popular cruises, this Sheffield Island–inspired gathering offers another way to connect with the organization’s mission in a relaxed and festive setting,” said Rick McQuaid, President of the Seaport Association.

 

This event is also a celebration of Norwalk’s deep-rooted oyster-farming heritage. The renowned Copps Island Oysters cultivated by Norm Bloom and Son are nurtured under the dock and then planted in the sandy bottom of Long Island Sound. The time-honored farming techniques used today have been practiced for centuries. The result? Oysters prized worldwide for their sweet, briny flavor and plump, tender meat.

 

If you’ve never tasted oysters literally fresh off the boat, this is your moment. Watch skilled shuckers expertly open each oyster before your eyes — setting them on trays with fresh lemons and a variety of delicious sauces. It’s culinary theater at its finest! Not an oyster lover? No problem. The evening will also feature a delicious spread of stationed appetizers catered by Seaside Sliders, along with craft beer and wine to complement the coastal cuisine.

 

With Long Island Sound as your backdrop and live music filling the early summer air, Docktails & Oysters blends fun, flavor, and philanthropy. It’s a chance to reconnect with friends, meet new faces, and celebrate the working waterfront that defines Norwalk’s character. Attendance is limited to just 200 guests, and the event sells out each year. Tickets are available online at https://www.seaport.org/docktailsandoysters2026.

 

For those looking to toast summer while supporting a cherished Connecticut landmark, Docktails & Oysters promises an evening that is as meaningful as it is memorable.