Malibu of the Midwest: Surfing in Sheboygan

By Cailly Morris

Standing waist deep in the frothy water, I stare at the 4-foot wave tumbling toward me. I pause, close my eyes and recite my mantra one more time — push, jump, stand up.

Push.

Jump.

Stand up.

Simple enough. An icy wave forms behind me, barreling toward my back. I take a deep breath and push off with my board, feeling the whoosh of the water graze my side.

Push.

Jump.

Wipeout.

Far from the exotic shores that lure international surfers to ride dangerous and impossible waves, I’m plunged deep into the swirl of Lake Michigan off the coast of Sheboygan, Wis., known as the Malibu of the Midwest. Surfing in Sheboygan is one of the state’s best-hidden secrets and is currently making me wonder — where the hell am I?

As I drive to the Lake Michigan coastline, I feel transported into a world where the sun-bleached, laid-back California surfer meets rugged beer-bellied cheese lover. Seven cars line the edge of the road with worn-in multicolored surfboards jutting from the roofs. Men stand outside each door, stripping down to nothing as they impressively pull up their jet-black wetsuits with ease and run toward the shore.

I envy their wetsuit abilities, as it takes me 10 minutes to get my first leg in the tiny mouse hole of an opening, and another five minutes to realize I’m actually shoving my leg into the armhole. After heaving and thrusting my body into the rest of my unforgiving wetsuit, I ask for help to shove my head through the suffocating hood. Catching my breath, I turn to look at myself in the mirror, and there I am — a bald seal, overheating in my rubbery skin.

For once, the cold air is a blessing.

“We practice safe surf here,” Sheboygan surfing aficionado Larry Williams says as I stand sweating in my body condom. “The Great Lakes are tremendously cold … so make sure that you are properly dressed. You wouldn’t go sled riding in a T-shirt and shorts, so don’t go surfing without a wetsuit.”

Larry is the definition of chill. He embodies the surfer mindset, and it shines through in his passion and admiration for the power of the Great Lakes. At 58, Larry and his twin brother Lee are the David Beckhams of freshwater surfing. Everyone looks to them for direction and inspiration. Growing up with Lake Michigan as their backyard, Larry and Lee were introduced to surfing at a young age.

“With 35 surfers in town, my brother Lee and I were within the top two or three surfers starting right off the bat,” Larry says, his eyes glistening with pride. “It was just something we were born to do.”

Their love affair with the surfing lifestyle is what led the brothers to develop the Dairyland Surf Classic, the premier freshwater surfing competition in the nation.

“It’s a celebration that summer is finally over, but it’s [also] the celebration that our surf season is finally starting up,” Larry says eagerly. I couldn’t have asked for a better surfing master to take me out in the water for the first time.

Larry is kind enough to lend me his legendary yellow and tan Dewey Weber surfboard, one of the most respected longboard brands in the country. I try to replicate every surf movie in existence by carrying my new companion Dewey over my head. No such luck. I can barely carry him at all, let alone raise him any higher than my waist.

When I enter the water and start walking toward the waves, my nerves finally settle in. The water doesn’t intimidate me — I’m actually a talented swimmer — but for some reason I begin to picture my surfboard knocking me unconscious and freshwater fish eating me alive.

“We’ve never had a reported shark attack, [but] we’ve had plenty of frostbite,” Larry says. That’s reassuring.

As the waves ripple toward me, I recount the past 30 minutes of explanation from my surfing coach on what to do when the wave hits the board: push, jump, stand up. Before entering the water, Larry gives a brief lesson on the anatomy of a wave so I know exactly when to push off from the water. My goal is to get on right when the base of the wave hits the tail end of Dewey, right when I feel him being lifted in the air.

Keeping everything my surfing guru told me in mind, I wait for my first wave.

“Here comes your wave,” Larry shouts. “Get ready!”

As the waves roll toward me, I repeat my surfing mantra again: push, jump, stand up. The wave hits the tail end of Dewey, causing him to rise slightly, and I push off hard and jump onto his center.

Push.

Jump.

Wipeout.

Years of yoga have not prepared me for the balancing skills needed for surfing. My body gains 20 pounds as the wave drags me under the water. Larry informs me I am positioning myself too far back, but before I can think about what I’m doing wrong — crash! Another wave. Dewey and I can’t catch a break.

I learn the importance of having a leash attached from my leg to my legendary friend. I feel like Tom Hanks searching for Wilson in “Castaway” as I rummage through the choppy water searching for Dewey.

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