The city has puzzled for years over how to resolve its reputation as a maze.

In the center of downtown Waukesha stands an intersection called Five Points. Drivers on Broadway, Main Street and Grand Avenue pause at stop signs and … try to figure out what to do next.

“You see, 50 percent of the population believes this is two intersections, and the other 50 percent are of the opinion it’s one,” Waukesha resident Mike Johnston wrote in a satirical 2011 post on his blog, The Online Photographer. “This means that no matter what you do, half of your fellow citizens think you’re being either ignorant or a jerk.”

It’s not just Five Points. If you’re used to street grids in Milwaukee and elsewhere, you might be baffled by Waukesha’s angle streets and five- and six-way intersections, particularly downtown. It’s enough to give a place a reputation.

“The old joke here is that the only reason people live in Waukesha at all is that they drove in and couldn’t find their way back out,” Johnston wrote.

Waukesha officials have heard it all but say the city’s reputation is outdated. They’ve been working for years to make it easier to get around.

Local lore claims Waukesha’s streets follow ancient Indian trails. However, historian John Schoenknecht says an 1855 archeological map by scientist Increase Lapham disproves that legend. Schoenknecht and others suggest the twisting Fox River more likely shaped the street pattern.

Driving became more complicated when city officials converted many downtown streets to one-way following a 1974 master plan, according to city project engineer Katie Jelacic. In 1982, downtown merchants successfully pressed for a gazebo in the middle of Five Points, thinking it would attract pedestrians, Jelacic says.

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Instead, traffic confusion peaked. Businesses pushed a positive spin with the slogan, “Get lost in the charm of downtown Waukesha,” Schoenknecht says. When Police Chief Russell Jack started as a patrolman in 1990, he says, officers regularly encountered wayward drivers, “especially on late shifts, especially when they were intoxicated.”

Recognizing the problem, city officials redrew the master plan in 1998, moved the gazebo to the riverfront in 2002, changed streets back to two-way and improved signs. Now, Jack and City Engineer Alex Damien say, traffic flows smoothly.

But Waukesha’s angle streets – and the city’s reputation as a bit of a maze – remain intact in the era of smartphone navigation. “People joke about it all the time,” Schoenknecht says.

“The Way in Waukesha” appears in the March 2019 issue of Milwaukee Magazine.

Find it on newsstands beginning Feb. 25, or buy a copy at

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