Northern Michigan’s waters are open and the warm winds are blowing.  That means sailing season—and the lake’s most prestigious race, the Chicago to Mackinac—will be unfurling before we know it. 

Want to experience the world’s longest freshwater open water race first hand?  We checked in with Chicago Yacht Club’s Greg Freeman, chair of the race, to learn how to chart a course toward crewing during the July 23-24 event, whether you’re a salty dog or a novice sailor.

 MyNorth:  The Chicago-to-Mackinac normally boasts a pretty broad range of sailors. Is that something unique to this race?

Greg Freeman: We feel very fortunate that our race attracts both family sailors and pro sailors and has been doing so for well over 100 years. But the fact is that the vast majority of the over 3,000 sailors in our race are amateurs that are racing for the fun and sport of the race. They race with family and friends and have a great time, competing in a one-of-a-kind race.
MyNorth: Should people looking to crew in the Chicago to Mackinac start looking now, even though the race does not begin until late July?

Greg Freeman: Yes, definitely. The sooner the better. Sail boat racing is a team sport and the earlier in the season the team begins to know each other and work together, the better off they’ll be during the race. You need to know everyone’s strengths and weaknesses and be able to plan your crew assignments based on this. Also, the more you sail together, the better you get at handling the boat and sails and of course, the more fun you have. Don’t wait.
MyNorth:  What would you tell more novice sailors about the fun and work that goes into crossing Lake Michigan?

Greg Freeman: I would encourage anyone who wants to race in the Mac, or to cross the lake, to get on a boat with an experienced crew, to watch and learn, to work hard and to listen more than you talk. Sailing is like any other sport – it has it’s own language, and there are many positions on a race boat and a lot for a novice to learn. But you can learn it with some patience and by putting in some time and effort. And don’t forget to bring some beer for the whole crew for after the race.

MyNorth: For folks who want to catch a ride, what’s the best advice you have for getting on board?

Greg  Freeman: I’d suggest the best way is to go to your local yacht club, sailing center, or even to a boatyard at this time of year. Talk to people and see who is looking for crew and who needs help getting their boat prepped for the season. Don’t be afraid to get your hands dirty because working on the boat now is the best way to earn a spot once it hits the water. Many clubs also have casual racing during the week in the summer. Find out when that is happening and head down to the club and look for a ride. Be friendly and helpful and you’ll get a ride for sure. Another option is to post your sailing resume on our website at Look for the tab called "The Race" and select "Crewing Opportunities." Skippers in need of crew can find you there. But please, don’t overstate your qualifications. Be honest because a Skipper needs to know what you can and can’t do and just because you’re new to sailing doesn’t meant you won’t get a ride.