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Road Trips | Madeline Island

Tour sea caves, take shots at Tom’s Burned Down Cafe and train for a 2.1-mile swim across Lake Superior on this tiny Wisconsin island.

 (Photograph: Cameron Wittig)
Photograph: Cameron WittigTom�s Burned-Down Cafe on Madeline Island
 (Photograph: Jon Dolias)
Photograph: Jon DoliasMadeline Island
 (Photograph: Jon Dolias)
Photograph: Jon DoliasBig Bay Town Park on Madeline Island
 (Photograph: Jon Dolias)
Photograph: Jon DoliasMadeline Island
 (Photograph: Jon Dolias)
Photograph: Jon DoliasPenny on the Town Park beach on Madeline Island
 (Photograph: Jon Dolias)
Photograph: Jon DoliasMadeline Island ferry
 (Photograph: Cameron Wittig)
Photograph: Cameron WittigBig Bay State Park on Madeline Island
By Marissa Conrad |

I’m at a divey waterfront bar on an island off the coast of northwoods Wisconsin when a stranger plunks down and introduces himself as August. August is clutching a bottle of Old Style—not his first of the day. He has come to tell me that the big, black dog wandering the patio would like one of my french fries.

The eager mutt, one of many who roam Madeline Island like characters in a Milo & Otis movie, gobbles several fries before disappearing; August moves on to ridiculing a recall walker sign attached to a nearby dock. (By the time you read this, Wisconsin residents may have voted their governor out of office in a history-making recall election.) For a drunk guy living on a 42-square-mile island with one grocery store, my new friend is surprisingly tuned into state politics.

I soon find out August lives on the mainland, but takes the ferry across Lake Superior often to drink at island haunts. The ride’s only 20 minutes, and, unlike on many small islands, the 302 full-time residents of Madeline seem to welcome visitors. (From Memorial Day to Labor Day, the island’s population swells to 1,500.)

“It’s more fun over here,” says another mainlander, still celebrating her 50th wedding anniversary of several weeks prior, as she shatters a shot glass. This is Friday night, the day before meeting August. So far today, my boyfriend,  Jon, his dog, Penny, and I have driven eight hours from Chicago to the port town of Bayfield, taken the Madeline Island Ferry Line (Washington Ave and Front St, 715-747-2051; $13 round-trip, kids ages 6–11 $7, cars $24) and checked in at the Inn on Madeline Island (641 Main St, 800-822-6315; rooms $150 and up), a plush alternative to renting a cabin or camping (info at Faint strains of country music and whiffs of a bonfire have led us to Tom’s Burned-Down Cafe (234 Middle Rd, 715-747-6100), an open-air bar with two potbelly stoves burning logs to fight off the mid-May chill.

A local named Bert tells us the bar burned down several times before owner Tom decided not to rebuild any walls, and to serve alcohol out of a tractor trailer backed up to the patio instead. He also says Tom’s was voted the second-best beachfront bar in the world, and during peak season hundreds of people line up to get in for live shows. This is before telling us he’s proud his 13-year-old can roll a joint, and trying to slip us a large helping of weed. (We decline.) We’re later told we shouldn’t believe much Bert says. The tractor-trailer part and at least one of the fires, though, are real.

Tom’s is part of a tiny main drag that has a few restaurants, one bookstore and a café that serves its iced coffee in clear Solo cups. Grizzled men in paint-stained sweatshirts sit under taped-up flyers sporting photos of Gov. Walker, captioned does this ass make my sign look big? It seems everyone here loves to talk politics. But mostly, they just love to talk. We’re welcomed with shots of a cheap peppermint schnapps called Dr. McGillicuddy’s, and we leave with roadies of Jameson and an invite to a 30th birthday party the next night, to be held in a hangar on Madeline’s tiny, private airport.

The combination of the whiskey and a California king bed makes for a dreamy night’s sleep. The next morning, we take Penny to Big Bay Town Park (2305 Town Park Circle, 715-747-3031), where we walk for a mile along the beach before settling in for a nap on the sand. Penny likes this a lot better than the hiking at nearby Big Bay State Park (2402 Hagen Rd, 715-747-6425; $10 per car), where heavily wooded trails leave her covered in ticks.

Lunch is gut-bomb sandwiches and heavy pours of Santa Margherita sauvignon blanc at the hopping Beach Club (817 Main St, 715-747-3955), where a young woman we met the night before invites us to linger for more drinks, and her boyfriend offers to bring us jars of his mother’s homemade jam.

The island’s “fancy” restaurant, where it’s still perfectly acceptable to wear flip-flops, is called Cafe Seiche (794 Main St, 715-747-2033), and an early dinner of almond-crusted trout and a vegan plate packed with pesto, brown rice and veggies is our best meal of the weekend. Then we drive to the airport for the party. Dozens of cars are parked haphazardly on the grass, and the hangar is a sea of cheap card tables, homemade desserts and pitchers of sangria. Twentysomethings chat happily with sixtysomethings as a man in the corner strums a guitar.

We meet the island’s lone schoolteacher, whose K–5 classroom has just eight students (after fifth grade, kids go to the mainland for school), and reunite with another of our pals from last night, a man with a parrot on his shoulder who has been coming to Madeline since 1960. This year, he’s training for Point to La Pointe, a 2.1-mile swim from Bayfield to Madeline on August 4. He turns out to live a block from me in Chicago.

Were the water warmer, we probably would have spent our weekend kayaking, canoeing and taking a motorboat tour of shipwrecks and sea caves—all the typical tourist activities of the island. But this trip was a welcome reminder that people make the place, and I’m going to remember the people of Madeline for years to come. That, and stripping naked in a state park parking lot so my boyfriend could check me for ticks.

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