I went up to Sheboygan for a race weekend on Lake Michigan, and I thought I knew wind. I didn’t. The lake has moods. It whispers, then it shouts. And somehow, I loved both.
Why Sheboygan, of all places?
Short answer: the lake. Long answer: the whole scene. The lighthouse. The long breakwall. Blue Harbor’s big blue roof. Gulls yelling. Kids with ice cream. Brats smoking on a grill by the club. It feels homey, but also a little wild. That knack for hosting on-the-water excitement isn’t lost on the pros—Sheboygan recently earned the 2023 American Power Boat Association Best Race Site Award for the inaugural Mercury Racing Midwest Challenge, underscoring how seriously the town takes its marine horsepower. For the full story on that exact Sheboygan adventure, you can read my windy, splashy, grin-soaked weekend recap where I lay out every tack and spill.
You know what? That mix hooks you.
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Race day feel (and those sneaky waves)
We sailed a 23-foot keelboat, borrowed from a local friend. Four of us. Simple setup. One main, one jib, and a kite for downwind legs. The wind sat around 12 to 16 knots, then popped to 20 in sharp gusts. The chop stacked up fast off the breakwall. Not huge, but tight and snappy. Like the lake was tapping you on the nose—over and over.
First start, we were late. My fault. I counted the horn, then lost track talking about the line bias. Classic. We crossed, ducked two boats, and slid into clear air. The breeze veered right. We tacked early and got a little lane. It wasn’t pretty, but it worked.
Second race, we nailed the start. Bow out. Flat sails. The boat felt light. Then a wave slapped the bow. Cold spray hit me right in the mouth. I laughed, then choked. That’s Lake Michigan for you—she gives and she takes.
What I used (and what didn’t love me back)
I’m big on gear, but I keep it simple. Here’s what I wore and how it went:
- Gill spray top: Kept the wind off my chest and shoulders. No leaks at the neck. A bit stiff, though.
- Zhik PFD: Snug and comfy. No rubbing under the arms. A win.
- Harken sailing gloves: Good grip, but the right seam rubbed my ring finger raw by Race 3.
- Merino base layer: Warm even when damp. Dry by lunch. Magic.
- Sun Bum SPF 50: Didn’t burn, even with the glare. Smells like summer.
- Cheap wool hat from Fleet Farm: Not cute. Very warm. I kept it.
I also clipped a small CamelBak to the rail with a carabiner. That may sound odd, but it’s easy to grab in a puff. No fumbling in a bag when your hands are busy.
I landed on that setup only after a season of experimentation; earlier this year I tried five kinds of boat racing and the crossover lessons shaped what ended up in my duffel.
Little moments that stuck
- A kid on the pier rang a cowbell every time a boat passed the mark. He was ruthless. We got a pity ring, I think.
- A seiche must have rolled in. Water level looked different by the third race. No tide here, but the lake can shift like it’s breathing.
- On the downwind of Race 2, we got a tiny spinnaker wrap. I froze. Then I took a breath, eased the sheet, and the wrap fell out like it never happened. Felt like a magic trick.
- We finished one race in third. The skipper kissed his glove and yelled, “That’s for the brat fry.” I’m still not sure what that meant. But I cheered anyway.
Those dockside cheers took me right back to the salty pandemonium of the lobster boat races in Maine, proof that boat-crazy crowds sound the same no matter the coast.
Shore stuff matters too
After racing, we walked the South Pier. I ate a brat with onions and mustard, because you have to. The sun dropped behind the town, and the lake turned silver. A band played near the boardwalk. Folks wore hoodies and boat shoes. Someone handed me a Spotted Cow. Yes, it tasted like a win.
Launch and parking were smooth near the marina. The volunteers were kind, which counts more than people think.
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What I loved
- The wind builds in a steady, honest way. You can read it on the water.
- The race committee ran clean starts. No chaos, just clear horns and flags.
- Short, tight courses. Not boring. Not too long.
- The local vibe. Friendly. Simple. Real.
What bugged me (only a bit)
- The breakwall can make a weird rebound chop. The waves bounce back. It’s clappy and messy.
- Gloves rubbed my finger raw. Tape would’ve helped. My bad.
- The water is cold. Even in summer. If you hate cold, layer up or you’ll pout.
Tips if you go
- Bring a spray top and a warm hat. Even if the sun looks nice, it’ll turn sharp.
- Bright tape your gear. Dropped my multitool on the dock and found it thanks to neon tape.
- Don’t over-trim. In puffy air, ease a hair and keep the boat flat. Flat is fast.
- Watch the right side near the pier in a building lake breeze. Pressure stacks there sometimes.
- Eat first. The chop will steal your energy. A brat after is great, but a banana before saves the day.
- If you’re sticking around, the Sonar Wednesday Night Racing series run by SEAS lets visiting crews hop aboard equal boats and spar against the Sheboygan Yacht Club fleet every week.
My quick take
Boat racing in Sheboygan feels honest. The lake tests you, but it’s fair. It’s loud, a little cold, and very fun. I came home tired, salty, and grinning like a fool.
Would I go back? Oh yeah. I’m already packing the wool hat. And yes, I’ll tape that finger.
– Kayla