Since COVID-19 has been wreaking havoc on my travel plans, I’ve been more focused and excited for the little trips that fill in the space in between bigger ones this year. Every summer, a group of my high school friends and I drive to Bayfield, Wisconsin to spend a week on Madeline Island in the Apostle Islands chain. Check out my YouTube video to see some of the beauty of the area, featuring footage courtesy of a gifted drone from my lovely wife. 🙂
Normally I don’t write about this trip because it’s annual and only a few hours from home. But come on, it’s 2020 so all bets are off. The following article is a deep dive into how the Mad Isle Boys plan and execute our annual debauchery weekend.
It’s been pretty much the same squad from high school that’s taken this annual pilgrimage to this shotgun-shaped island on Lake Superior. It’s evolved from a more rugged camping experience to a bit more of a glamping one now. We may have traded in our flimsy tents and second-hand camping gear for a buddy’s uncle’s cabin now that we’re into our 30’s. But, the appreciation for the natural beauty of the area and all-around tomfoolery that ensues is still unchanged.
This trip has always been a chance for us to spend a few days away from home and pretend we’re still 18 year old idiots. Only difference is this year we took COVID-19 tests before heading out!
THE PLANNING
As a frugal miser, one of the parts I love about this trip is the low impact it has on my wallet. With just a few hours drive, food and lodging split 4-5 ways, and lounging being the primary activity, the cost is generally low. The past few years we’ve used the Splitwise app which has been really useful for dividing up expenses, especially the ones I personally excuse myself from like beer (or Truly Seltzers this year… again, we’re into our 30’s). We’ve evolved (somewhat) from Doritos and cheese puffs to high class snacks more becoming of young gentlemen. Like beef jerky and marshmallows.
Part of the fun of the Mad Isle Boys is anticipation that starts with the grocery shopping the night before we leave. Each Mad Isle Boi is responsible for cooking a meal or two. There aren’t too many requirements other than one dinner be grilled steak and our beach lunch be smoked whitefish, both of which we pick up from Louie’s Finer Meats on the drive from the Twin Cities to Bayfield.
This year we also decided to go the rental car route. It’s practical to try to squeeze the squad into one car, since the ferry to Madeline Island from Bayfield charges per vehicle. This year, we used Turo to rent a car big enough to house five dudes and their weekend stuff. I had used Turo on a separate trip with my wife and it’s a very smooth process. Long story short, you rent cars via an app from actual people. This way, you skip the whole weird hours and weirder employees of places like Hertz.
Beyond grocery shopping and renting the car, planning is pretty stress-free for this trip. Even for one as meticulous as me…
GETTING THERE
It’s just shy of a four hour drive from the Twin Cities where we all live to Bayfield WI. This is the town where you catch the ferry to Madeline Island. There is a northern route that takes you past Superior, WI, as well as a southern route. We usually take the southern route up (to stop for meats & liquor at Louie’s in Cumberland, WI) and then take the northern route back home for variety.
Once you’re in Bayfield, you’ll head to the ferry port in the southern part of town.
As I mentioned, you’ll pay by the car. If you’re frugal and into walking or biking, it is a cheaper ride. It runs every hour or so, but check the schedule at https://madferry.com/ferry-schedule to time your arrival. We always seem to have drama in the car trying to make a time… as if another ferry won’t leave within the hour.
Once you’ve paid and the grouchy ferry bouncers guide your car onto the ferry, you’re off on a 25-minute ride to Madeline with great views of the town and the water. After, you drive off the ferry and have landed in La Pointe, Wisconsin. La Point is the “downtown” (air quotes within air quotes) of Madeline Island.
THE DIGS
As I mentioned, for years we camped on this trip, always at a campground near Big Bay Town Park. The past couple years, we’ve booked the weekend at my buddy Isak’s uncle’s cabin. It’s situated at a cliff’s edge which gives a great vantage of Lake Superior and the southern half of Madeline Island. You can check out his cabin on VRBO. It’s even prettier in person though.
If you’re a little more rugged and willing, there are a lot of campsites at Big Bay Town Park. However, if you’re planning to go in summer make sure to book early because it does fill up.
SO MUCH ROOM FOR ACTIVITIES
We split a fair amount of our time with lounging, eating, and beer pong, but I’ll spare you the details on that. I’ll rather regale you with what you can do if you’re feeling active and social… which we often aren’t when we’re at Madeline.
We always spend a few hours of each weekend at the long beach that starts at Big Bay Town Park. There’s a sizable parking lot that funnels you towards a stairway down to the beach.
We spend a lot of time at the beach playing Spikeball and eating our Louie’s smoked whitefish. The waterfront is beautiful, but if you’re not familiar with Lake Superior, even at the warmest of times it’s pretty frigid. You’re usually good for one quick dip in for the whole weekend.
At the beach, there is also an opportunity to rent kayaks and canoes. You pay in a cash box on the honor system and can launch into the lagoon behind the beach. It’s big enough that I’d venture to call it a lake. With calm waters, this is a peaceful hidden gem on the islands where you can see painted turtles and loons doing their thang.
One other tradition for the Mad Isle Boys is cliff jumping at Big Bay State Park. Check Googlemaps and drive to Big Bay Point for the beautiful classic jagged-point cliffside views of Lake Superior. There’s a short trail from the parking lot that leads you along the cliff’s edge to an obvious jumping point. No injuries from cliff jumping to report to date, as the biggest jumps we do are maybe ten feet. However, again, the water is cold enough to shrivel up even the manliest men. So it’s usually a jump followed by a frantic doggy paddle to a quick exit.
For nightlife, the young sinners of Madeline Island head to Tom’s Burned Down Cafe. As the non-drinker / babysitter / den mother of our group, I roll my eyes at even writing about this since it’s my least favorite part of the trip by FAR. But, I indulge my self-poisoning friends. There is an undeniable charm to this outdoor bar. Goofy puns on small signs line the walls of the place as you’re served drinks in little generic plastic cups. There’s often live music (not saying it’s masterful) and there’s always friendly faces.
There are also really nice hikes for the more nature-inclined visitor throughout Madeline Island. There is a lot of private property on the island, but the majority is walkable park and forest land for you to explore. We usually take a hike or two each year, venturing up to the northern part of the island.
THE EATS
As indicated in the planning section, we usually bring the majority of what we eat and drink for the weekend. There isn’t a ton in terms of food offerings in Madeline. There are a few restaurants in town (that I’ve never been to) and we do often stop for breakfast and coffee at Mission Hill Coffee House, but I’d recommend bringing your own food for both variety and cost purposes. This year, I decided to buy myself a second steak while the rest of the squad had a porky dinner, and a small individual one for myself at the little grocery store in La Pointe robbed me of $20. Criminal!
THE WATCHOUT – GAS
One additional pointless drama we often find ourselves in (after rushing to catch the ferry) is getting gas throughout the weekend. We don’t drive a ton other than to the beach, hikes and Tom’s (barf). So, this shouldn’t be that big of a deal. But it’s really difficult to get gas at Madeline for some reason.
There’s an old-timey looking place that LOOKS like a gas station in downtown La Pointe. I’ve never seen it open so am convinced it never opens. Long story short, fill up in Bayfield before you get on the ferry. Even if you’re in a fake rush like we are.
WORTH A VISIT
Like I said, we do this trip every year. You could interpret that as boring, OR a testament to how much we love the place. There’s something about putting your car on a boat to get to an island that makes you feel like you really escaped everyday life for a bit. That, plus the overall natural beauty of Lake Superior, makes this a trip that we plan on taking annually for a long time to come.
