Milwaukee Volunteers join for Schooner Fest
Written by Staff
September 15, 2025
Labor Day weekend, Denis Sullivan returned to Gloucester, Massachusetts, to take part in the 41st annual Gloucester Schooner Festival. The event is a beloved celebration of tall ships that draws vessels and ship enthusiasts from across the region. For Denis Sullivan, the festival was more than just a chance to join the Parade of Sail and schooner race. It was also a chance to reconnect with her roots.
Denis Sullivan amidst many other ships during the parade of sail
Built in Milwaukee and still deeply cherished there, Denis Sullivan welcomed a contingent of 12 volunteer crew members from her home port to help sail the ship and share her story. Their presence was more than symbolic. It was a living reminder that the bond between ship and city remains strong even as Sullivan now spends her seasons voyaging between New England and the Caribbean.
From the moment they arrived, the volunteers were immersed in ship life. “From the moment we were invited aboard by First Mate Rudy, we felt we were in good hands,” shared Barbara and Dick Prodehl, who joined for the weekend. “That night, we were treated to fireworks right at our doorstep. After a good night’s sleep in our cozy berth, we mustered with the crew and volunteers, many from Milwaukee, before setting the sails. Despite the off-and-on rain, we had our best sail of the long weekend.”
Their story is echoed by others who carry special ties to the ship. Stacy joined the volunteer crew after watching all four of her children participate in overnight programs aboard Denis Sullivan. Carolyn and Alex sailed to Gloucester with a particularly meaningful connection. They had been married aboard the ship earlier this year.
The weekend was filled with memorable moments. Visitors climbed aboard for deck tours, crew and volunteers worked together to raise the sails, and the parade was a thrill, surrounded by dozens of ships. Autumn Crow, one of Sullivan’s regular crew members, recalled, “I went aloft to loose the raffee during the parade of sail, and it was so cool to be surrounded by so many boats of all kinds while aloft.” Later, on the return voyage to Boston, Autumn had the joy of guiding volunteer crew aloft for the first time. “It was amazing to see their excitement and sense of accomplishment at the top.”
Deckhand Autumn Crow aloft during the schooner race
Simon, a Milwaukee volunteer, enjoys the view from aloft
Across the weekend, more than 1,500 visitors came aboard Denis Sullivan for deck tours and sails. With her Milwaukee volunteers at the heart of the action, the ship felt both rooted in her origins and alive with new energy.
For World Ocean School, this connection is central. Milwaukee is a special community to this ship; events like this festival are how we continue to curate and strengthen that connection, even as Sullivan carries students and communities across the East Coast and Caribbean.
As the harbor emptied of schooners and the ship made it back to Boston, the Milwaukee crew stood together on deck. It was a reminder that while Denis Sullivan now roams far from her birthplace, she will always carry Milwaukee with her.
Milwaukee volunteers take a group photo before they leave ships company
