One of the oldest racing trophies in the sailing world was up for grabs at the Queen’s Cup Race, held annually on the Great Lake starting from the South Shore Yacht Club (SSYC) since 1938.

Close to 150 sailing ships caught the wind on June 23 as they competed across 76 nautical miles of freshwater for a trophy commissioned in 1853, just 7 years after the City of Milwaukee was incorporated. The finish line in South Haven, Michigan took about ten hours to reach.

“The down side of things is that when you have a prevailing wind, from this side of Lake Michigan to the other side, it’s great when you’re going over,” recalls John Liebenstein, who has sailed in Bay View for nearly half of his 80 years. “But coming back can be a bit of a problem as the waves sometimes get really big. If the crew is inclined to be sick, it can be scary. We’ve had a couple of those, where we got down to only two people left who could work and weren’t immobile from seasickness. In terms of the race itself, we only one once but we’ve been competitive in every race.”

Starting in groups by boat-class division, waves of sails stretched from the Milwaukee side of the Lake in the late afternoon, to arrive after midnight and into the early morning on the Michigan side.

“I sail at the South Shore Yacht Club on Wednesday nights. I’m on a sailboat crew, but I own a power boat,” said Gary Johnson. “I think you’ll actually see a lot of people like that. The majority of power boaters just don’t want to put in all the work of sailing. They prefer driving somewhere, to get there and relax. Sailors don’t mind making the effort needed to stay out on the water all day sailing.”

Johnson has piloted power boats for 40 years, is on the SSYC Board of Directors, and has been involved with the Queen’s Cup for the past 11 years. The Milwaukee Independent photographed the prestigious race for hours from onboard Johnson’s chase yacht. The images of this Photo Essay try to present the expanse, challenges, and amazing experience of participating in the nautical event.