Regattas

The 86th sailing of this overnight race sails across Lake Michigan from South Shore Yacht Club in Milwaukee, WI, to Muskegon, MI. Competitors will navigate approximately 66 nautical miles, often contending with shifting winds and varying weather conditions on the open waters of Lake Michigan. Sailors compete for the chance to win one of the oldest trophies in yacht racing. The event is not only a competition, but also a celebration of camaraderie and the enduring spirit on sailing tradition. 

The race will feature a diverse fleet of sailboats, with classes for a wide range of participants, from seasoned racers to cruising enthusiasts. Muskegon Yacht Club will host the post-race festivities, welcoming competitors to celebrate their accomplishments.

Day 1 - Friday, August 1, 2025, 1:00 – 7:00 pm
Chieftain Cup Regatta is sponsored by the Pentwater and Ludington Yacht Clubs.  Activities begin in Ludington on Friday with a gathering of skipper’s and crew, a skipper’s meeting, and the start of the Chieftain Cup Leg #1 race to Pentwater.  Following the race, we’ll welcome all participants and members of both Clubs to enjoy a party and music at Pentwater Yacht Club.

Day 2 - Saturday, August 2, 2025, 1:00 – 4:00 pm
On Saturday, the race continues with a morning gathering of skipper’s & crew, the skipper’s meeting, and the start of the Chieftain Cup leg #2 race back to Ludington. 

The Bloomer Cup is an annual sailboat race hosted by the Ludington Yacht Club (LYC), typically held in September, and named after Bob Bloomer, a brother of Betty Ford.  The race is held off of Ludington Harbor.  The 2025 Bloomer Cup is expected to be held in September, with the exact date to be determined.  The LYC will likely host a weekend of events, including cocktails on Friday and the Bloomer Cup race on Saturday.  Check back here later for further details on the Bloomer Cup Regatta as they are determined.