Sailboat Racing in West Michigan: The Thrill of the Wind and Waves
West Michigan has a vibrant sailboat racing scene that brings together seasoned skippers and newcomers alike. From the midweek excitement of Wednesday night races to the high-stakes weekend regattas, the region offers plenty of opportunities to experience the thrill of competitive sailing. Whether you're a seasoned sailor or looking for a way to get involved, there’s a race—and a breathtaking sunset—waiting for you.
Weekly Racing Action
For those looking to get on the water midweek, Wednesday night races in Holland and Muskegon are a staple of the local sailing community. These races provide an excellent way to hone your skills, meet fellow sailors, and enjoy the camaraderie that comes with the sport. Whether you're crewing on a fast-paced one-design or a classic cruiser, the thrill of the race and the golden hues of the setting sun make every outing unforgettable.
Regattas: The Heart of Competition
West Michigan also plays host to a variety of events and weekend regattas that attract sailors from across the Great Lakes. Among the most popular are:
The Anchorage Cup – A fun and competitive race between Holland and Grand Haven, open to a wide range of boats and skill levels. Anchorage Marina hosts a post-race party with dinner, awards & live music.
Tripp Cup – A challenging race from West Michigan to Milwaukee that tests both strategy and endurance, bringing together some of the best sailors in the region. The 2025 race will depart from Macatawa Bay Yacht Club on June 25.
Queen’s Cup – One of the most prestigious races on Lake Michigan, drawing a fleet of skilled competitors for an exhilarating run across the water. Racers leave Milwaukee and race back to West Michigan
MBYC Ladies Keelboat Regatta – Taking place on June 14, this regatta at the Muskegon Yacht Club is a fantastic event that highlights the skills and competitive spirit of female sailors, promoting inclusivity and excitement on the water.
The Big Boats: Ultimate Challenges on the Great Lakes
For those seeking the pinnacle of Midwest sailing, the big races offer a test of skill, teamwork, and endurance:
Chicago to Mackinac Race – One of the most legendary freshwater races in the world, spanning over 300 miles from Chicago to Mackinac Island. The race starts July 19, 2025 and culminates with a party on the island.
GL52 North America Series – A high-performance racing circuit featuring some of the fastest and most advanced sailboats competing on the Great Lakes. Competitive racing and comraderie go hand-in-hand with the GL52 fleet, with many amateur teams sailing alongside highly pro teams
How to Get Started: Join a Crew!
One of the best things about sailboat racing in West Michigan is that you don’t need to own a boat to participate. Many skippers are looking for crew members—whether you have experience or not. Show up at a local sailing club, connect with race organizers, or simply walk the docks before a race and express your interest. It’s an incredible way to get on the water, learn the sport, and become part of an enthusiastic and welcoming community.
Sailing isn’t just about competition—it’s about adventure, teamwork, and the simple joy of being on the water. Whether you’re racing hard for the finish line or just soaking in the sunset over Lake Michigan, there’s no better way to experience the magic of sailboat racing in West Michigan.
Photo credit: Vega Aerial