Former SS Keewatin Employee Turns Tour Guide, Relives Youth

Doug Cunningham, now 79, has returned to the SS Keewatin in Kingston as a tour guide, bringing with him memories of his youthful days aboard the historic ship. The SS Keewatin, an Edwardian era vessel, is currently docked on the shores of Lake Ontario and serves as a popular tourist attraction. Cunningham first encountered the ship at the age of five while traveling to his family’s cottage in Port McNicoll during the 1950s. It was during those childhood visits that he vowed to one day work aboard the vessel.

In 1962, his dream became a reality when he joined the crew of the Assiniboia, the sister ship of the Keewatin, as a night steward. His responsibilities included checking fire points and serving sandwiches to crew members. Just two years later, Cunningham’s aspirations were fully realized when he accepted a position as a waiter on the SS Keewatin, a job he initially found limiting. However, he soon discovered the challenges and rewards of working in the ship’s dining room.

Cunningham recalls his first experience serving on the Keewatin vividly, stating, “I went by the officers’ table, and I almost dumped the tray! You could see all the guys just waiting for the tray to fall. But I managed to get it.” He humorously adds that navigating rough seas often felt like a dance, saying, “I probably added 50 new dance steps to my repertoire just trying to get to each table.”

His role was demanding, with limited spots available for placing trays, and he quickly learned the intricacies of French service. The extensive menu included juices, soups, appetizers, main courses, and desserts, which made memorization essential. Some waiters even resorted to writing menu items on their fingers to avoid confusion. Instead of memorizing every dish, Cunningham found success promoting specific items, particularly the Georgian Bay Lake trout, which he would claim was freshly caught. “I would usually end up getting most of the people to order Georgian Bay Lake trout!” he recalled.

Cunningham’s duties didn’t end with serving; he was also responsible for cleaning and resetting tables, as well as tidying the dining room. During his time working on the ship, he earned approximately $400 a month, plus tips, which he estimates would be around $3,200 today. “That was pretty good. You could buy a brand-new car for $1,800,” he noted.

Reflecting on his experiences, Cunningham fondly remembers the lively atmosphere on the ship, especially when American college girls visited during summer tours. “You can imagine what the ship was like with all these girls,” he said with a laugh. He also recalled the challenges of fitting into the small beds on board, highlighting the camaraderie among the young crew.

Now, in 2025, Cunningham has taken on a new role, serving as a tour guide for the very ship he once worked on. “Every time I take a tour, I look at it this way: where can anybody actually go back to the 1960s and relive it?” he remarked. Working three days a week, Cunningham finds joy in sharing his unique experiences with visitors, including those who also worked on the ship in its operational years.

The Great Lakes Museum, which oversees the Keewatin, values Cunningham’s contributions immensely. Claire Notman, the museum’s visitor experience manager, emphasized the importance of his lived experiences. “That personal experience, that lived experience is something you can’t find very often in a museum,” said Notman. She noted that Cunningham’s enthusiasm and people skills have made his tours highly regarded among visitors.

“Most of us can’t give that. We can give the script and anecdotes that we’ve heard, but we can’t do that on our own,” Notman added. As the only guide with firsthand experience aboard the Keewatin, Cunningham offers a unique perspective that enriches the visitor experience.

For those wishing to explore the SS Keewatin, it is advisable to book tours in advance, as they run only from May to October. With Cunningham at the helm of the tours, visitors are sure to leave with a deeper appreciation for this historic vessel and the vibrant stories it holds.