#street-view-road-trip

The farther west you travel from Chicago, the less obvious it becomes where Chicagoland actually ends.

The city does not simply stop. Suburbs thin out. Housing developments become islands. The spaces between them widen. Decorative streetlights give way to utility poles, and then, almost without announcement, the landscape belongs to corn.

That makes DeKalb County, Illinois an interesting place for a random Street View road trip.

It sits about 63 miles west of Chicago, covers roughly 633 square miles, and had an estimated population of about 102,000 in 2025. DeKalb and Sycamore provide the county's main urban centers, Northern Illinois University brings a sizable college presence, and yet enormous portions of the county remain unmistakably agricultural.

The DeKalb County History Center describes agriculture as one of the defining threads of the county's history, and that becomes obvious almost immediately on Street View.

But there was something else I kept noticing.

The countryside here did not look especially rough.

It looked organized.

Maybe I had simply stumbled onto an unusually tidy collection of roads, but scene after scene had the same peculiar quality: trimmed lawns, clean gravel drives, bright barns, sharply defined fields, buildings that looked freshly cared for. Coming from central North Carolina, where rural landscapes often feel looser and more accumulated over time, I found the contrast striking.

The randomizer has sent me to a county where my first interpretation was wrong often enough to become the story.

Musselshell County, Montana initially looked, through Street View, like an essay about absence.

A gravel road runs toward the horizon with almost nobody on it. Fields lie brown beneath a tremendous sky. Utility poles march away until perspective swallows them. In Roundup, an old sandstone school that looked lively in 2011 appears boarded up fourteen years later. Farther down the road, the cheerful sign for an old café disappears between Street View visits.

It would be very easy to arrange those photographs into a familiar story about rural America slowly emptying out.

Then I started checking.

According to the U.S. Census Bureau, Musselshell County is not shrinking at all. Its population was 4,730 in the 2020 census and was estimated at 5,582 in 2025, an increase of nearly 18 percent. About one in five residents is under 18.

The boarded-up school has an even bigger surprise waiting behind it.

So perhaps the interesting question here is not, What went wrong with Musselshell County?

It is: How much can we really know from a photograph?

Quick facts

• County: Musselshell County, Montana
• County seat and largest city: Roundup
• Population: about 5,580
• Land area: about 1,869 square miles
• Population density: 2.5 people per square mile in 2020
• Established: 1911
• Named for: the Musselshell River
• Landscape and economy: ranching, dryland farming, coal mining, small communities and the broad Musselshell River valley

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

The randomizer has finally found a loophole.

Or at least, that was my first thought when it landed on Barceloneta, Puerto Rico.

This series is supposed to be a random journey through the counties of the United States. Puerto Rico does not have counties. It has municipios, 78 of them, each with its own mayor and municipal government.

But according to the U.S. Census Bureau, those municipios are officially treated as county equivalents.

So Barceloneta counts.

And after wandering around it on Street View for a while, I am very glad it does.

Barceloneta sits on Puerto Rico's northern coast, west of San Juan, with a population of a little over 22,000 people. It was founded in 1881 from territory that had belonged to neighboring Manatí and Arecibo. Its landscape reaches from the Atlantic coastal plain into greener interior country, but one of the municipality's defining modern features is industry. Barceloneta has long been associated especially with pharmaceutical manufacturing, enough to acquire the nickname La Ciudad Industrial. The Census Bureau estimated its population at 22,316 in 2025, while EnciclopediaPR traces the municipio's origins to its foundation in 1881.

That industrial history matters, because the first Street View scene I found is almost aggressively familiar.

Google Street View

If you dropped me into this image with the location hidden, I am not sure I would guess Puerto Rico.

There is a McDonald's. There is a Taco Bell with Pizza Hut attached. There are traffic lights suspended over a wide multilane road, cars turning into parking lots, utility wires, palm trees clipped into corporate landscaping, and a large modern commercial building across the intersection.

This is the running index for Road Trip by Randomizer, a virtual travel series where I use a random U.S. county generator to pick a county or county-equivalent, then wander through it using Google Street View.

This page is not a ranking of which places are “best,” most beautiful, or most important. It is a ranking of encounters: which places grabbed me most through Street View, which scenes lingered, and which virtual roads made me want to keep looking.

A lower score does not mean a place is dull. It may only mean I did not stumble onto its best road yet. The map has a way of keeping secrets.

Scores are subjective and intentionally approximate. Ties are allowed.

There are 3,245 counties and county-equivalent places in the United States, and the randomizer has already begun behaving suspiciously like a storyteller.

First it sent me to Gosper County, Nebraska, a quiet county in the plains. Then it sent me to Yalobusha County, Mississippi, larger, greener, and more Southern in a way that felt both distant and familiar. And now, for the third stop in this series, it has sent me to Coos County, Oregon.

This is the most populous county the randomizer has given me so far. It is also the first coastal county. And visually, it is operating on a different level entirely.

Coos County sits on the southern Oregon coast. Its county seat is Coquille, its largest city is Coos Bay, and its population is somewhere around 64,000, which makes it much larger than either of the first two counties in this little experiment. It was founded in the 1850s, named for the Coos people, and stretches from Pacific beaches and bays into forests, river valleys, and old interior roads.

That last part is what surprised me most.

I expected the coast to be beautiful. Oregon has a reputation for that. But I did not expect the county to feel so geographically compressed, as though several different movie locations had been folded into one map square. One minute, I was looking at fog, cliffs, beach grass, and an old car by the water. A little later, I was standing virtually on a broad beach beside sea stacks and a happy orange dog. Then I was inland, following a narrow road through green forest, sunlight, moss, boulders, flowers, and a small creek that looked suspiciously prepared to transport a hobbit.

There are 3,245 counties and county-equivalent places in the United States, and already, after only two spins of the randomizer, I am beginning to suspect that this project is going to be less about “discovering hidden attractions” and more about learning how much of America exists in a state of deep roadside quiet.

The second county it gave me was Yalobusha County, Mississippi.

Yalobusha sits in north-central Mississippi. It was founded in 1833, named after the Yalobusha River, and has the unusual distinction of having two county seats: Water Valley and Coffeeville. Its population is a little over 12,000, which makes it much larger than the first stop in this series, Gosper County, Nebraska, but still small enough that the county feels, from the Street View roads, mostly rural, dispersed, and watchful.

What surprised me first was not how unfamiliar it looked, but how familiar.

I expected Mississippi to feel much farther away than it did. Instead, many of the roads could almost have been roads I know from North Carolina: nondescript pines pressed up along the shoulder, reddish dirt pull-offs, modest houses set back from the road, trailers half-swallowed by vegetation, the occasional patch of kudzu performing its slow green takeover. The details differ, of course. Every place has its own weathering, its own light, its own roadside grammar. But the broader visual language was unmistakably Southern.

There are 3,245 counties and county-equivalent places in the United States, which means that even before leaving the chair, America is already too large to hold in the mind at once.

So I decided to let chance drive.

The idea is simple: use a random county generator, land somewhere in the United States, then poke around Google Street View looking for whatever the roads are willing to reveal. Not the famous places first. Not the postcard places. The opposite, really. Places that might never appear on an itinerary unless randomness, that tiny digital tornado, drops you there.

The first county it gave me was Gosper County, Nebraska.

And Gosper County, at least from the roads I wandered, does not immediately throw open a carnival of landmarks. It is not trying to impress the passing stranger. It is rural Nebraska in the nearly Platonic sense: flat fields, pale roads, enormous sky, utility poles, farm buildings, windbreaks, and the horizontal patience of land used for growing things.

There is a strange pleasure in that kind of landscape. At first, it looks empty. Then the emptiness starts making demands on your attention.

The roads are spare. The county feels visually quiet in the way a room feels quiet after everyone has gone home. There are long stretches where the main event is the distance itself. Cornfields and stubble fields reach outward in all directions, and the horizon seems less like a boundary than a habit the earth has kept for a very long time.