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Letter from a “semi-rural” fantasy zone

What I learned when the Town of Middleton’s local politics exploded.

The summer before fourth grade, I moved to the Town of Middleton, on the far western edge of Madison and just beyond the City of Middleton. My family moved to a brand-new house in a brand-new subdivision on a street named after the family farm it’s built on. On the school bus, a kid said that his parents hated the new neighborhood. At the time I was offended. 

Nearly two decades later, that moment feels like foreshadowing. 

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Long-time residents of the Town of Middleton are obsessed with the idea of being “semi-rural.” It’s a patently false definition of the landscape today, but it persists because here people don’t want to be Madison. They don’t want to live in “the city.” Read: They don’t want to pay city taxes.

Today I’m living in that same house in the same subdivision on the same street named after the same family farm it’s built on. I absolutely could not afford to live here on my own if I wanted to (which most of the time I don’t, but then I go out in my parents’ giant yard and kind of do). But that’s the point, I suppose. This is a place for only a certain kind of people. Upper-middle-class people. White people, mostly.

I can’t imagine that many people get the chance to have one clear moment when the curtains get pulled back on all the lies their childhood town taught. Changes, particularly in a sprawling, decentralized suburban town, happen subtly. But I kind of got to have that moment of clarity at a town board meeting in 2017. When I realized that the traditionalist model wasn’t the loudest voice in town anymore, and that the semi-rural facade had already crumbled. I imagine other towns on Madison’s fringe, and around the edges of fast-growing cities and suburbs throughout the county, have had similar reckonings. 

In the early 2000s, the City of Madison and the Town of Middleton set up an agreement defining boundaries between the two municipalities for the next 30-odd years. The goal of the plan, as stated in said plan, is to: “Best promote public health, safety, morals, order, convenience, prosperity or the general welfare, as well as efficiency and economy in the process of development.” I don’t know exactly what it means to develop morally, but suburbia doesn’t really feel like it.

Sometimes this is the kind of town that belongs in a silly sitcom. There’s been a years-long fight over a field of sunflowers, for example. Other times it feels caught between a mythical small town past and an inevitable suburban future (if not present).


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The politics of this place are messy, mostly quietly so (our neighborhood association doesn’t allow political signs), but occasionally loud. It’s that way in which Upper Midwest politeness has the tendency to blow up when privilege is called out.

The Town of Middleton overwhelmingly votes for Democrats these days, but there are loud voices of conservatism here too. In the spring of 2017, our first election since Wisconsin, and the nation, elected Donald Trump president, two town board members and the town chair were up for re-election. 

It was an unusually tense election for the town. In 2015, the state legislature passed a law stating that Dane County townships could choose to opt-out of county zoning. The law appeared to be a push by conservative town leaders throughout the county to deregulate zoning and give more power to private interests in land development. And our Republican-controlled state legislature is never one to miss a chance to stick it to Dane County. 

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Town of Middleton Board Member Tim Roehl, who was up for re-election that spring, lobbied hard for the zoning bill at the state legislature. An Isthmus story published during our 2017 election season began, “Tim Roehl is sick and tired of being bossed around by big-city folks.”


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It was clear that Roehl wanted to opt out of county zoning. He’d also been part of a push to make the requirement for town citizens to vote in favor of opting out merely advisory. That in particular made write-in candidates step forward. The election felt a bit like the only chance the people of the town might get to vote on whether we separated from the county on zoning or stayed in it.

One write-in candidate, Richard Oberle, challenged Roehl for his seat, while Cynthia Richson ran as a write-in against the incumbent board chair, Bill Kolar. Oberle and Richson distributed their messaging via flyers left on mailboxes and in-person, door-to-door canvassing. I don’t remember any other town election where multiple people knocked on our door. It was pretty hard to avoid being aware of the drama.

The loudest argument the write-in candidates made was that the town currently had no mechanism or staff expertise to competently manage zoning, so it should stay within the county’s jurisdiction. They also spoke about prioritizing conservation and public use of land.

If I’m honest, I know very little about zoning. The town, for reasons unfathomable to me, is almost totally residential. There’s a Kwik Trip, a quarry, a ski jump, some great parks, and a couple of lingering farms, but other than that it’s concrete and plastic siding as far as the eye can see. Roughly 3,000 single-family homes and not one grocery store.

But for those of us who valued thoughtful, sustainable development, it still seemed a better option to remain under county zoning than to put development and land use into the hands of a more conservative-minded board.

Oberle and Richson both won. As write-ins, that was a major upset. 

A few weeks after the election, the town gathered for a meeting in which the new board members would be installed and we, the residents, would take a vote to gauge resident interest in opting out. There were too many attendees to fit in the building. According to my tweets from the meeting (the proper historical record), it was announced that “We’re at room capacity, and instead of moving people they’re just bringing in a few firefighters and telling us where the exits are.”


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In the packed meeting room, Bill Kolar, the outgoing board chair, took the time to berate us for not voting for him. When Richson tried to speak, Kolar screamed, “I DON’T RECOGNIZE YOU,” and blamed her for ruining his reputation. Someone in the crowd yelled “C’mon man.” But Kolar kept going. 

I don’t know that I’ve ever felt such a heavy awkwardness. My brother described the meeting as the most uncomfortable moment of his life.

When the outgoing chair was done haranguing everyone, we were all handed small pink slips of paper with a yes and a no on them. The question was not written on the piece of paper and I don’t remember how it was worded, but overwhelmingly the town’s residents chose to remain under the county’s zoning jurisdiction. 

For me, those dramatics felt like the last gasp of the traditionalist “semi-rural” obsession of the town. The past was over. 

At that point, the town had been changing for a while. It grew quickly, as farmland sales became increasingly profitable. But it’s hard to grasp ideological change when driving through a new neighborhood. I never looked around at the new houses and thought, “Oh this isn’t the conservative town I grew up in.”

It wasn’t until I was packed into that meeting room with a few faces I recognized, but way more that I didn’t, that I realized this was a new kind of place—a place way less willing to reject the city than ever before (even while people are still avoiding the taxes). Since that meeting, more fields have been turned into homes, and the population has grown more liberal and even a tiny bit more diverse.


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It feels likely that—even if it takes until the cooperative agreement expires in 2060—at some point the town will be Madison. It certainly won’t be the first of Madison’s vestigial border towns to go. In 2022 the Town of Madison will be attached to the City of Madison and the City of Fitchburg. The Town of Blooming Grove will be fully annexed into Madison by 2027. And private landowners, particularly of farmland, in unincorporated areas, are able to apply for their land to become part of Madison.

I imagine for some people and some communities, the incorporation into the “big city” will be painful. I don’t feel that way myself. Everything I have to be nostalgic about—like the tree fort down the street, the open cornfields—is already gone. And, god forbid, maybe we’ll even get a grocery store within walking distance or a connection to a bus line. Whenever it happens, I only hope we’ll be ready to be good city residents.


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