Race to Mackinac

On Saturday, over 300 sailboats will take part in the famous 333-mile race from Chicago to Mackinac Island, the world's oldest and longest freshwater regatta. The Chicago Yacht Club's Race to Mackinac, which was founded in 1898, has competitors sail from Chicago at one end of Lake Michigan to Mackinac Island in Northern Michigan at the other end of the lake.

One entry into the race, Esmeralda, comes from as far away as Japan. But rumor says the boat to watch is Genuine Risk. Owned by a former Chicagoan, Randall Pittman, this boat is expected to shatter Roy Disney's Pyewacket record set in 2002. As for Chicagoist, we'll be cheering for Measure For Measure and Vayu, where our friends will be part of the crew.

You can get involved by heading over to Navy Pier on Saturday morning to watch the Parade of Boats. The procession of sailboats decorated with ceremonial flags will glide by on their way to the race's starting point.