By day Madeline Island is a quirky beach getaway. At night the magic begins. Usually, when people think of a beach vacation they imagine working on their tan while lying on golden sand. While Madeline Island most definitely has that aspect of island life going for it, the shores of Lake Superior aren’t the only places where The Island comes alive when the sun goes down. Tom’s Burned Down Cafe is where locals and tourists alike come together on Madeline Island to celebrate another day in paradise.
Night time is my favorite time on Madeline Island. The sound of the waves and the call of the loons, the absolute darkness, the mind-blowing view of the night sky, the tranquility; it’s magical. But before we head back out to the beach for skinny dipping under the Milky Way, we’re gonna go into town and head to Tommy’s, which, like everything on The Island, you really just need to experience to fully understand (and appreciate). A few years ago I invited a friend from high school and her husband to come camping at Big Bay with us. When we took them to Tom’s she said, “I thought it was weird that you go to a bar when you’re camping, but now I get it.”
Tom’s Burned Down Cafe is exactly what the name implies. Shortly before the official opening of what was then known as Leona’s, a small fire broke out that quickly spread (aided by the fact that the firetrucks had just drained their tanks to prevent them from freezing), and the whole place burned to the ground.
While surveying the charred remains of where his life’s work and all his money once stood, as if to add insult to injury, the beer delivery for the grand opening showed up. Tom, a lifelong Islander, was broke AF and his dream had just literally gone up in smoke. Instead of breaking down, he did what any Islander would do. He opened that goddamn bar out of the back of his car, changed the name from Leona’s to Tom’s Burned Down Cafe, and bam! History was made.
Today Tom’s is legendary. It stands on the repaired remains of Leona’s original floor, and consists of multiple trailers and hastily constructed buildings adorned with lights, lanterns, various graffiti-like signs and sayings, and is surrounded by eclectic art. There are even showers in the bathrooms that are open for public use. Just pay the bartender, or drop some cash in the box on the bathroom door if the bar is closed. Yes, I’m serious. Why? Because Tommy’s.
At night the whole compound lights up and is host to all walks of life, both human, and of the animal kingdom. In fact, I’ve never been there at a time when there was not at least one dog roaming around. One time there was an old dude walking around with a bird on his shoulder. Yes, a real live bird. Why? Because Tommy’s.
The year round Islanders mingle with the summer people and tourists, and the phrase, “No shirt, no shoes, no service,” is definitively not the policy at Tom’s Burned Down Cafe. Indeed, one could show up stark naked, and I’m not sure it would even be an issue. The smell of cannabis is frequently (and delightfully) in the air, and on summer weekends it’s the one place on Madeline where you can always find live music.
In Wisconsin people who are underage can not only go into a bar, but can even be served alcohol as long as they’re with a parent. Since my daughter was nineteen and was about to enter her sophomore year of college, I decided she was ready for a night out at Tommy’s.
Olivia wasn’t sure what to expect. She knew that it was a crazy looking bar that the adults loved to go to, and that we always came home fairly intoxicated. She had been there during the day, but that is not even remotely the same experience. A couple of years ago I went to Tom’s Burned Down Cafe with my brother and Zach. I was ordering shots of vodka, but the bartender was pouring quadruples, and after two of those I was wasted. Chris and Zach got me back to the campground safely, and the rest of the night is pretty much a blur. I do remember waking up in the middle of the night to pee, but that’s about it. When Olivia woke up in the morning, she came out of the tent and said, “Mom, I had to wear your flip flops, mine smell like pee.” As it turns out, I had not, in fact, left the tent to pee, though I most definitely had gone. . . on my daughter’s fucking shoes. Why? You got it, because Tommy’s. Somehow I didn’t win a Mother-of-the-Year award that year. Weird.
Liv was pretty excited (and probably a little nervous her mom was gonna get wasted and piss on her shoes again–which I am pleased to say did not happen) as we drove into town with Zach. Kim and the rest of the gang were meeting us at the bar, and after stopping on the way to take pictures at the Madeline Island School of the Arts, backlit by an absolutely spectacular sunset, and a very aggressive deer (did you know deer hiss? Me either), we parked the car in town and headed into Tom’s Burned Down Cafe.
Most of The Island closes around 8:00 in the evening. The town of La Pointe was quiet when we pulled in, but Tommy’s, as always, was hoppin. The whole place was lit up, fire already roaring in the fireplace, as we walked into the bar. We claimed the prime spot: the big, round table under the tiki umbrella, got some drinks, and settled in.
I love being at Tom’s. There’s such an incredible, positive energy there, and sharing it with my daughter was particularly entertaining. I was glad that not only was her first legal drink with me, but it was also on Madeline Island, and at Tommy’s. So much cooler than my first legal drink, which I literally don’t remember as I was pregnant with Olivia when I turned 21.
We went up to the bar and Zach got the first round. When he asked Liv what she wanted, she froze for a second. So unaccustomed with ordering at bars, she hadn’t even thought about what she would want to drink. So many options! After a brief pause where I imagine a zillion thoughts went through her mind simultaneously, she settled on a Jack and Coke. A classic choice.
Though Tom Nelson, owner and badass, doesn’t recognize me until I tell him who I am (I was a child when he knew me), as soon as he realizes I’m “Pastor Dale’s daughter,” I’m greeted with a huge smile, a warm hug, and a tale of how much he respected my dad. “He would come in here and we would have these long talks. Your dad is a cool guy. Tell him Tommy says hello.” It always makes me feel at home.

If you’re looking for high class and a five star drink menu, and are incapable of letting loose for a night, Tom’s Burned Down Cafe isn’t the place for you (and you and I would not be friends). But if you enjoy really getting to know the local culture when you travel, or quirky, fun bars, a trip to Madeline Island isn’t complete without a stop at Tom’s Burned Down Cafe.
After an hour or so of talking and laughing with the whole group, most of our people were ready to call it a night. Zach, Olivia and myself, however, ordered another drink. As usual, the crowd was eclectic and having a great time. Prime people-watching at Tommy’s, there’s a little bit of everything: a group of drunk, middle aged women, a group of drunk, middle aged men, a group of barefoot hippies, the obviously wealthy “boat people,” who’ve docked their vessel at the marina for the night, a mom breastfeeding her baby, one really drunk lady (which has been me on more than one occasion). It’s got something for everyone.
The three of us sat there for a few more drinks before deciding to head back in for the night. Liv’s first experience at Tom’s Burned Down Cafe was perfect. It’s a memory she’ll always have, and will tell her kids about someday. And isn’t that what life’s all about? Making memories and sharing them with the most important people in our lives?
Though I could stay at Tom’s all night, leaving is always made easier by what awaits us at Big Bay Town Park. The night sky from Madeline Island will blow your mind and leave you in literal awe. But for that we will have to wait for the next installment, which I promise will not take months for me to post.
Thank you for reading! Check out my other blog posts for more stories of my Ladycations, and don’t forget to subscribe to stay up to date on the latest tips, trips and tales. And, as always, stay chill and keep hiking, my friends!