Bayfield/Madeline Island, WI August 2023

Estimated read time 8 min read

Next up is a couples trip with our dog, that we just returned from yesterday, so I want to write about it while it’s fresh in my mind. We have a cabin about 2+ hours away from Bayfield, WI, so it’s easy for us to take a short trip from there without having to drive almost 6 hours in one day. Bayfield is just such a fun little area to visit, full of shops, restaurants, and apple orchards you definitely want to explore in the fall. Pair that with a short ferry ride to Madeline Island, which hosts one of my favorite places to stay, and our favorite dive bar in all of Wisconsin, and you’ve got a perfect 3 night getaway!

We started out by driving to Bayfield and picking up lunch from a little restaurant we enjoy called Manypenny. We ordered food to go and sat along the shore of Lake Superior eating our broiled whitefish sandwiches, while the dog sniffed around and enjoyed the fresh air. Next, we walked along the fishing pier (I swear one of these years I’ll actually remember to bring a fishing pole with me) and the playground area. Then, we headed back to the main street to peruse the shops. We enjoy buying little touristy trinkets like magnets to signify where we’ve traveled to, candles, coasters, t-shirts, anything that catches our eye really. Even if you don’t want to buy things like that, it’s just fun to walk around.

The ferry to Madeline Island leaves every half hour, and it costs us $65 for a round trip with 2 adults, a dog, and a car. It’s fun to get out of the car and enjoy the lake breeze, and take a few photos. Once you’re in La Pointe, on Madeline Island, there are more shops to walk through, a few restaurants, a bar, and lots of shoreline to explore.

When we go here, we rent from The Inn on Madeline Island, although we’ve never stayed at the actual inn. They also rent out little cottages a short distance inland, which are the perfect place for us to stay with our dog. A large king sized bed, a huge couch for the dog to sleep on, a patio in the front and the back (one used to contain a fire pit, but there was a burning ban on the island so the pits had been removed, much to our dismay) and my personal favorite…the BEST bathroom in all the world. This bathroom is as big as the bedroom in my actual house, the shower could hold probably half a dozen people comfortably (if you were comfortable showering with 5 other people, that is) contains THREE shower heads, and there is the most glorious bathtub. The barn door opens up into the living space, so you could bathe while watching TV, or have the fireplace on.

Other things making this cottage one of my favorites is the wildlife. Open up the door at any point and there will likely be a deer or two staring at you. Keep the windows open at night to let in a cool breeze, and you will hear the loudest coyotes howling, that sound like they are right outside your window looking in.

The first night we were there, we did not have a neighbor in the cottage next to us, so we were comfortable leaving the dog alone in her crate. We went to the actual inn to have dinner there. Monday night was “Crabby Monday,” so I enjoyed a half pound of snow crab legs and a drink. We got back to our cottage just in time before the skies opened up with a heavy downpour. We turned on a show we like, and played cards while enjoying a few drinks at home.

The next day we had lunch at a restaurant called the Beach Club. One warning when it comes to Madeline Island—do your research on which restaurants are open when you go. Many of them have very limited hours, and finding food options can be difficult. There were restaurants that we thought would be open, which turned out not to be. We ended up eating at the Beach Club for 3 meals—which is not to say that it’s a bad thing. The food is good, and the patio is cute and dog friendly. I must strongly advise, however, that you absolutely DO NOT go to the only coffee shop on the island. The coffee is horrendous. I brought my own creamer from home, and it literally curdled in the coffee. Husband and I both took a couple of sips, decided it was the worst thing we’ve ever tasted, and dumped it out. Fortunately there was an art gallery across the street that had a Nespresso machine, and we got coffee from there. The inn supplied us with a Keurig machine, which is fine by me, but I deeply regretted not packing my French press.

Following lunch, we took our dog to Big Bay State Park, which honestly, barring the fact that there are no palm trees in Wisconsin, is arguably one of the best beaches around. We did some hiking, met some friendly people, and let the dog take a dip in the lake.

After tiring out the dog, we drove back into town to visit the best dive bar—Tom’s Burned Down Cafe. I won’t go into the history of this place, but feel free to look it up yourself. I’ve heard a lot of people say, “it’s not a bar; it’s a whole experience,” and that is absolutely true. There is excellent reading material posted all over the place. There’s a drink for everybody—cocktails, macro beers, craft beers, NA beers, you name it. They have live entertainment there regularly. You can even scratch your name into a wall or a chair or wherever you see fit, so that you can be a part of it indefinitely. It’s hard to even describe the place. Just go there.

On our 2nd full day, we got gyros and cheeseburgers from the local food truck, bought a couple of canned Starbucks drinks from the grocery store, and then made our way to the Big Bay Town Park. The town park is free, unlike the state park, and has a ton of great beachfront for your beach day. You can even rent kayaks and canoes there, which we didn’t do because our dog would never sit still. There is a boardwalk that takes you into the state park, but for some reason you can’t go into the state park portion with your dog from that side.

After our beach day, we went back to Tom’s Burned Down Cafe, then back to the Beach Club for dinner. One of my other favorite parts about this island is that the locals get together and play croquet on the lawn every single day. It is fun to watch them. Then we went back to the cottage early, had a bottle of wine, and I enjoyed a night in the tub.

The next morning we took the ferry back to Bayfield, and again had breakfast at Manypenny. It turned out that this was a dog friendly restaurant, so we could actually eat there instead of in the park. Afterward, we visited the rest of the stores that we hadn’t gotten to on the way to the island. My personal favorite store was a bookstore that must be new, or I’d have certainly visited on previous trips. I bought a book written by a local author. It even takes place on Madeline Island and mentions Tom’s Burned Down Cafe.

Of course, when you are visiting Lake Superior, you must take some delicious whitefish home with you. There are several fish markets in the area. We loaded up and hit the road.

The final portion of our trip was visiting all of the apple orchards in the area. You can pick up a map and basically follow them in a circle. Our favorites are Erickson’s Orchards—they make the best apple cider donuts. The Bayfield Apple Co. has a neat selection of wares, and you can feed old bruised apples to the pigs there. At Hauser’s you can taste 5 different flavors of apple cider and take your favorites home with you. There are probably around a dozen farms you can visit, but those are our three favorites.

That concludes our trip, but as a side note, there are many things I would also consider doing if we didn’t have our dog along on this trip. You can rent mopeds and drive them around the island, charter fish, rent kayaks, camp, and explore many more restaurants in the Bayfield area. Some day I would absolutely love to go see the Apostle Island Sea Caves, whether by cruise or by kayaking. Hopefully sometime I can rewrite this article with photos of some more of my bucket list items!

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