Road Trip by Randomizer: Kewaunee County, Wisconsin

The randomizer has sent me somewhere that looks, at first, almost suspiciously well behaved.

Kewaunee County, Wisconsin sits along the western shore of Lake Michigan, just southeast of Green Bay and immediately south of the much better-known Door County peninsula. About 20,800 people live here today, spread among farmland, small towns and roughly 30 miles of lakeshore. The county seat is Kewaunee; its largest city is Algoma, population about 3,200. U.S. Census Bureau data puts median household income at about $82,700, somewhat above Wisconsin as a whole.

This is dairy country, farming country, manufacturing country, fishing country and, along the lake, increasingly vacation country. Agriculture remains conspicuous enough that a drive inland quickly becomes an inventory of barns, silos and improbable expanses of corn. The 2022 Census of Agriculture still treats Kewaunee as a substantial agricultural county, while local tourism promotion leans heavily on fishing, beaches, trails and the Lake Michigan waterfront.

In other words, this is not primarily some sleepy retirement colony that happens to have flowers.

There is real economic machinery underneath the hydrangeas.

And yet, after wandering around Kewaunee County on Street View, the machinery was not what stayed with me.

What stayed with me was a man in a Rolling Stones shirt standing astride a bicycle with two dogs.

Quick facts

• County: Kewaunee County, Wisconsin
• County seat: Kewaunee
• Largest city: Algoma
• Population: about 20,800
• Region: Lake Michigan coast, northeastern Wisconsin
• Established: 1852
• Known for: dairy farming, agriculture, manufacturing, fishing and lakeshore tourism

The unofficial ambassador

This may be my favorite human encounter the randomizer has produced so far.

We are on a quiet rural road. Evergreen trees wall off the background. A yellow DEAD END sign provides a certain philosophical clarity. And directly in front of the Street View car, an older man has stopped his bicycle with two large dogs on leashes beside him.

He is wearing a Rolling Stones T-shirt.

Everybody is looking at Google.

The dogs appear intrigued. The man appears mildly suspicious. Google has arrived uninvited in their cul-de-sac and, for one frozen instant, all parties are forced to negotiate the situation.

There is a particular northeastern Wisconsin character that I kept imagining while wandering around this county: part fisherman, part biker, part homeowner with a meticulously organized garage, somebody who might own both a Harley-Davidson and a perfectly serviceable pedal bicycle and see absolutely no contradiction between the two.

Obviously, one photograph cannot tell us this man's politics, occupation, temperament or preferred brand of bratwurst. Maybe he is a socialist orchid collector. Street View anthropology has limits.

But it can capture posture.

And this photograph has posture to spare.

It is an unexpectedly good introduction to Kewaunee County because the place repeatedly gave me this combination of orderliness and independence. The lawns are usually cut. The houses are generally cared for. Nobody seems particularly interested in impressing anybody.

Things simply occupy their territory.

Including the dogs.

The garden house that disappeared

A little farther along Lake Michigan, in the city of Kewaunee itself, I found something stranger.

Here is Lakeshore Drive in 2013:

And here is approximately the same place a decade later:

At the water's edge sits a tiny shed or garden house.

In 2013 it looks almost absurdly wholesome. The roof is clean. The latticework is visible. Flowers surround it, but the structure remains clearly in command of its botanical surroundings.

Ten years later, vegetation has launched a coup.

The building has been swallowed in green.

At first I interpreted this as neglect. That is one of the dangerous games Street View encourages. A weed appears, paint peels, grass gets long, and suddenly you find yourself writing the economic obituary of a community you have never visited.

But look around the rest of the property.

The landscaping still appears intentional. The waterfront itself is neat. Nothing else about the scene screams abandonment. And Kewaunee County is not an especially impoverished place. Its recent median household income is above the statewide figure.

So perhaps this is not a shed losing a battle with nature.

Perhaps this is the garden winning.

The distinction is surprisingly difficult to make from a photograph.

That became one of my favorite questions about this county: when does overgrowth mean decline, and when does it mean abundance?

A clipped hedge says somebody cared.

An enormous flowering vine also says somebody cared.

They just have radically different opinions about what caring should look like.

The waterfront itself raises another question. Kewaunee looks richer from Lakeshore Drive than its small population might make you expect. Boats sit in the harbor. Houses face the lake. Gardens are cultivated. There is enough disposable income here for the scenery to acquire polish.

Tourism certainly plays a role, especially along the Lake Michigan shore, but Kewaunee County is not being held aloft by tourists alone. Farming remains deeply embedded in the county's landscape and economy, and the region also participates in northeastern Wisconsin's manufacturing economy. The result is a place where productive rural land and surprisingly comfortable waterfront living can exist within a few miles of each other.

Milk, machinery, marinas and begonias.

Wisconsin has assembled a diversified portfolio.

Welcome to Alaska

Then, halfway between Kewaunee and Algoma, the road begins announcing that we have reached ALASKA.

Not Alaska the state.

Alaska, Wisconsin.

Its strange name is a nineteenth-century souvenir. The community emerged not long after the United States purchased Alaska from Russia in 1867, and Wisconsin place-name histories trace its name to the newly acquired Alaska Territory. A commercial pier was also established here in 1867 as Kewaunee County's Lake Michigan lumber trade expanded.

This means that for people living here in the late 1860s, “Alaska” was not yet the familiar shape on the corner of an American map.

It was news.

The United States had just bought an enormous, remote northern territory from the Russian Empire, and somebody in Wisconsin apparently looked at their little settlement beside Lake Michigan and thought:

Yes.

Alaska.

Nearly 160 years later, the name survives in giant white letters beside Highway 42.

Barely.

What fascinated me here was not the sign itself, but the historical Street View sequence. In earlier imagery, the letters seem distinctly maintained, sitting cleanly above the grass.

In the newest image I found, nature is beginning to eat the word.

A few more good Wisconsin summers and visitors may arrive at L S A.

Does that mean somebody stopped caring?

Maybe.

Or maybe the mower was scheduled for Thursday.

This is where Street View becomes unexpectedly interesting as a historical document. Google keeps driving through ordinary places every few years and, almost accidentally, creates a visual record of things that nobody would otherwise think worthy of archival photography.

The tree gets larger.

The shed turns green.

The sign disappears into the grass.

A business changes hands.

A house gets painted blue.

History usually arrives dressed as presidents, wars and factory closures. Street View catches history in increments of shrubbery.

The friendliest political fault line in America

Keep following Highway 42 north and eventually you reach Algoma.

The entrance could have been commissioned by the Wisconsin Department of Small-Town Charm.

An iron arch announces DOWNTOWN ALGOMA. A marina sits beside the road. An American flag rises near the water. A church steeple punctures the skyline. There are flowers, lamps, tidy sidewalks and just enough old industrial architecture to keep the scene from becoming a Hallmark movie set.

Nothing is flashy.

Everything seems maintained.

My first reaction was that this looked like civic pride in its purest Midwestern form.

My second reaction was more complicated.

In the United States of the 2020s, even an American flag sometimes feels politically legible. You start noticing the flagpole, the bunting, the veterans' memorial, the pickup trucks. The brain begins attempting partisan archaeology.

Is this MAGA country?

That instinct is not entirely irrational. Kewaunee County has generally favored Republican presidential candidates in recent elections.

But Algoma itself throws a wrench into that tidy story.

In 2020, Joe Biden won Algoma by six votes.

Six.

In a city of more than 3,000 people, you could fit the presidential margin into a minivan.

That extraordinary political split eventually brought national attention. In 2024, The New York Times profiled Algoma as “the most divided place in America.”

And suddenly that pleasant downtown arch becomes more interesting.

Because nothing about the photograph looks divided.

There is no red half of the street and blue half of the street. There are no ideological customs checkpoints at the marina.

The same flag belongs to both sides.

The same harbor belongs to both sides.

The same person who thinks the country is being destroyed by Republicans may buy coffee from somebody who thinks the country is being destroyed by Democrats, then both of them complain about Wisconsin road construction.

That may be one of the stranger truths hidden inside contemporary American political maps.

Maps color entire counties red or blue because maps need colors.

Real places do not.

Sometimes democracy looks like a town split almost perfectly in half walking beneath the same decorative arch.

At the end of the pier

Finally, I followed the county back to Lake Michigan.

And here Kewaunee County stops feeling quaint.

The Kewaunee Pierhead Lighthouse stands at the end of a long concrete pier extending into the lake. The current structure dates to 1931, and it remained staffed until its automation in 1981, though navigational lights had operated around Kewaunee Harbor for decades before it. Today, preservation work continues around the historic light station.

In photographs from shore, it looks picturesque.

From Street View, it looks like a level from Myst.

The path is enormous and empty. A metal seam runs down the concrete like a rail toward the lighthouse. Water occupies almost everything else. There are no souvenir shops, no café tables, no crowd posing for photographs.

Just concrete.

Lake.

Sky.

Lighthouse.

The perspective exaggerates the isolation until the building seems less like something constructed by engineers and more like an object placed there because the game requires you to solve it.

There is probably a brass lever inside.

Somewhere beneath the pier is a book containing coordinates.

Do not turn off the generator.

After the gardens and dogs and lawns and downtown arches, this is an unexpectedly eerie place to finish.

But perhaps it is the right one.

Kewaunee County initially presented itself as an exceptionally tidy piece of Wisconsin: farmland inland, attractive towns on the shore, boats in the harbor, flowers beside the sidewalk.

Then the random details began accumulating.

A Rolling Stones cyclist guarding a dead-end road with two dogs.

A garden house disappearing beneath vegetation.

An Alaska being reclaimed by grass.

A beautiful little city so evenly politically divided that six votes once separated the presidential candidates.

And finally a lighthouse waiting alone at the end of a concrete path, surrounded by enough blue-gray water to erase the Midwest entirely.

That is why I keep doing these random county trips.

A map makes places look like administrative subdivisions.

Street View makes them weird again.