Fri. June 5 - Sun. June 7 | 2026
Baileys Harbor, WI
The Schoolhouse Weekend
A few lessons in exploration from a classic Wisconsin harbor village.
Stay two nights in an exquisitely reconstituted 1917 schoolhouse, complete with a principal’s office.
Restore yourself on Lake Michigan, aboard a floating sauna.
Dine at a farm-to-table favorite where you may — though it is not guaranteed — find yourself seated in the library room.
As always, your stay, meal and local experience are all bookable in one click.
Get the full story for the weekend.
Pictured: original plans for Baileys Harbor District #1 Schoolhouse, courtesy the Schoolhouse Inn
Where you’re going: To a thread of a town set along Lake Michigan, with many categories of wonder.
Why here?
Photo by mheisel
Travel is about learning something, we think.
Not in a study-it, homework kind of way. The best kind of travel feels like an effortless introduction to the particulars of a place. You accumulate small injections of interesting newness, and it’s all mostly incidental and accidental. It just gets into you.
Read on or
Photo by Ida Whitney
We’re going to overstretch the metaphor probably, but Baileys Harbor, Wisconsin, is a kind of elite liberal arts degree of a town: it does not specialize, it is a comprehensive escape education that criss-crosses all sorts of subject matter. Even the location — it’s on the ‘quiet side’ of the peninsular Door County — has a name that suggests a wide-open do-anything feeling.
There is the very charming harbor part, but then there is also the village, but then also the hayride to the lighthouse (well, there are three lighthouses) and the sweeping natural beauty, and the floating sauna that bobs you atop Lake Michigan.
The harbor itself was a discovery. In 1848, a ship captain, Justice Bailey, found his vessel amid a thrashing Lake Michigan storm. As the local historical society puts it, “The storm was so severe that he risked entering an uncharted harbor; luckily, he found it to be of sufficient depth.”
The town has possibly the perfect place to base yourself for all this taking-in: a 1917 schoolhouse that’s enjoying a whole new life as an impeccably restored inn. Much more on this place to come.
So take off to Baileys Harbor this weekend. Let it teach you something about good, slow, meaningful exploration.
Like Captain Bailey, you will find it’s absolutely of sufficient depth.
Photo by August Schwerdfeger
This weekend in Baileys Harbor, discover…
The stay.
Room photos by Ida Whitney
In working schoolhouse days
Baileys Harbor Schoolhouse Inn
Sometimes your stay — the inn or hotel or lodge or whatever it is — ends up being the defining feeling of your whole trip. We’re not sure why that is exactly.
A static room, nice as it can be, should really have much more trouble competing with your real, underlying travel rationale: the museum or the monument or the trail or the slopes, or whatever the true why of going might have been in the first place. Because the idea is you stay over, because you have to, to see the thing you want to see. But a great inn can edge all of that right out of the frame when you think back.
This place is lying in wait to do that to you.
It was built 108 years ago as Baileys Harbor District #1 Schoolhouse. Out of use and in disrepair by the mid-1990s, it was a local family, the Peils, who saved the old school from demolition and alchemized it into an inn.
Now it’s Kristen Peil and her husband, Caleb Whitney, and their daughter Ida, who are dreaming new purpose into these classrooms. There are six stayable rooms, with fun vestiges of their origin-story cropping up all over (we love the original principal’s office door, especially).
High ceilings, long schoolhouse windows shooting up. A fantastic sense of place, with whispers of old algebra alongside a bright new life.
The family, mid-restoration.
You’re reserved and pre-paid for Friday and Saturday night. Two travelers.
The day.
Photo via Kiln Floating Sauna, Instagram
Kiln Floating Sauna
We love that this exists, and especially that it exists in the middle of Lake Michigan.
Kiln is the creation of Zoe Lake, who was inspired by the pervasive sauna culture of Scandinavia. The boat, as it were, is an authentic cedar-fitted sauna with temperatures pushing 180°.
This wonderful, peculiar, steamy little craft spends the winter season in Chicago off of Navy Pier (where it has been absurdly popular), and in the summer months it docks right here in Baileys Harbor.
“There’s something really magical about being on water,” Lake told CurbOnline. “You can feel the boat move, you can hear the boat move — you’re taking yourself out of the element of being on land.”
We’re including a public sauna session for two this Saturday. Just arrive.
The find.
Photo via Nathan Nichols & Co.
Nathan Nichols & Co.
Another local discovery with a meta-discovery story at its center.
The showroom for this exquisitely curated furniture and design company (although that doesn’t really capture all they do), is set in a well-preserved 19th-century structure in the heart of the village. Before the place became its current tasteful accumulation of things, the building served as a bakery, a pharmacy, and a barbershop (a faint ring, still visible on the floor, is evidence of a once-barber chair).
The store’s namesake owner, who has since passed away, was a native East Coast-er who fell in love with this town instantly, and bought the building where the shop still thrives, on the same day he found it.
The food.
Photo via Chives Door County, Instagram
Chives Door County
The food is great, the ceilings are a dark pressed tin (we are suckers for pressed tin ceilings, always), and of course Chives has its famous library room. Or possibly the library has a Chives room, because there is a substantial commitment to the shelving here.
We cannot guarantee that you will be seated next to these books, although we are working on it. But you certainly have reservations for Saturday evening at 5:45pm.
Here is the menu. There are Beef Cheeks Bourguignon, with spätzle and white cheddar. We had no conception of what spätzle might be, but can now report that it is a soft egg dumpling of a sort, with origins in Germany and Austria.
Dinner for two, already taken care of. $175 food and drink credit. Order right off the menu.
The tucked away.
Photo by WHS, Maritime Preservation and Archaeology Program, via Wisconsin Shipwrecks
The Wreck of the Peoria
Just seven feet beneath the surface lies the Peoria, which was shipwrecked — twice — off this coast.
Time #1 was in 1880, when the ship, laden with a cargo of lumber, ran aground along a reef near Baileys Harbor Lighthouse. The crew was rescued, and the vessel was later dislodged and repaired to sail again.
Off it went to Milwaukee, where it promptly sank, was raised, then patched and put right back into service.
The long-serving Peoria returned to Baileys Harbor in 1901, again during a storm, and again, disaster. Despite dropping both anchors, the ship was blown up onto shore and beached. All the crew were rescued, but this time the craft was unraisable.
The lower portion of the ship is still right there, just below the surface, embedded in the sediment.
The evening mood.
Photo by James Jordan
Whispering Lanterns
You’re rolling into town at exactly the right time for Door County Maritime Museum’s Lighthouse Passport Days, which is a sort of open house for all 11 of the county’s lighthouse sites.
In particular, there’s Cana Island, which is hosting Whispering Lanterns, a nighttime, bonfire-side chat with the keeper of the light, who will share tales from the island’s long history, all underneath the revolving beacon beam.
This one isn’t pre-paid, but just let us know you’d like to include it, and we’ll make sure you have tickets (they’re $25 per person).
Book it all in a click.
This Overnight includes:
Your two-night stay at Baileys Harbor Schoolhouse Inn. Reserved for two on Fri. June 5 and Sat. June 6, 2026.
A float for two in the Kiln Sauna on Saturday, June 6. 75 minutes of steam, a-bob on Lake Michigan.
Dinner for two at Chives on Saturday evening at 5:45pm. $175 food and drink credit; order right off the menu.
Images in our stories may be sourced from publicly available material. All rights remain with their respective owners.