A Visitor's Guide To Waukesha: Everything To Know Before Your First 25 Minutes Behind The Train
Whether you're here for the county fair, a wedding at the Rotunda, or because your GPS gave up somewhere on Highway 164, welcome. This guide will not get you downtown any faster, but you will understand why.
WAUKESHA — So you're visiting Waukesha. Congratulations. You have chosen, or been assigned by a wedding invitation, one of Wisconsin's finest county seats, a city of roughly 71,000 people, one navigable roundabout (contested), and a downtown street grid designed by someone who we can only assume was being chased.
What follows is everything a first-time visitor needs to know. Locals may also read it, though they will claim they didn't.
The One-Way Streets: A Warning
Downtown Waukesha operates on a one-way system that reverses direction block to block, in a pattern that has never been successfully explained. Broadway goes one way. St. Paul goes the other way. The street you are on goes whichever way you are not currently driving.
Do not trust your GPS, which will recalculate four times in three blocks before going quiet in a way that feels personal. Do not trust the locals either. A lifelong resident will give you confident directions, watch you drive off, and then remember the part they forgot. This is a tradition.
The street you are on goes whichever way you are not currently driving.
— This guide
The accepted technique is to circle the block until the block lets you in. Budget 15 minutes. If you see the same boutique's "closing sale" sign three times, you are doing it correctly. The sign has been up since 2019. The boutique is doing great.
The Train: Please Read This Section Twice
A freight line crosses Broadway downtown, and freight trains use it with the confidence of something that weighs 14,000 tons and knows it. When a train is crossing, traffic stops. This is normal and takes several minutes.
Sometimes, however, the train stops. Not the traffic. The train. It will pull onto the crossing, come to a complete halt, and sit there, occasionally for up to 30 minutes, while it thinks about whatever trains think about. There is no announcement. There is no schedule. There is only you, the crossing arm, and time.
Here is the single most valuable sentence in this guide: the only way under the tracks is the Newhall Avenue underpass, on the south side, between West Avenue and Grand Avenue. Locals guard this information the way other cities guard restaurant recommendations. You will know a true Waukeshan by the fact that they are not in the line of cars on Broadway. They are on Newhall. They did not tell you about Newhall. Now you know about Newhall, and you owe this newspaper accordingly.
The East Avenue Roundabout
Waukesha's newest roundabout opened on East Avenue to great fanfare and immediate confusion. City officials have offered a key to the city to the first driver who navigates it correctly on the first attempt. The offer remains unclaimed. The roundabout has so far recorded 847 partial entries, 203 full stops from vehicles waiting for it to be "their turn" in an intersection that does not have turns, and one vehicle that entered and, as far as anyone can document, has not exited.
Our advice to visitors: yield on entry, signal on exit, and do not make eye contact with anyone who has stopped completely inside the circle. They are working through something.
Where To Eat
You will eat at Culver's. This is not a suggestion so much as a description of events that will occur. Order the ButterBurger, take the number, and understand that the drive-thru line wrapping around the building is not a sign of a problem. It is a sign of a community in agreement.
For groceries, there is the Piggly Wiggly, which locals call "the Pig" and which you should also call "the Pig," but not on your first visit, because it has to be earned.
If you are here during the county fair, be advised that the question of whether funnel cake or cream puffs better represent Wisconsin values is currently tabled until conditions improve, and visitors are asked not to reopen it. Order one of each and say nothing. Everyone will know what you mean.
Local Customs
The Packers are not a preference here. They are a load-bearing assumption, like gravity or the train. If you are from Illinois, you may be asked, politely but with genuine concern, how things are going down there.
Residents conduct neighborhood affairs primarily through Nextdoor, where a car you have parked legally will be photographed, discussed in a 34-reply thread, and eventually identified as belonging to someone's nephew. Do not take this personally. The car "didn't look right." No further explanation is available.
If you find yourself on Backslide Way, drive 25 miles per hour exactly and park a full 12 inches from every driveway apron. A 70-year-old man with a radar gun and a YouTube channel is documenting you, and his footage speaks for itself.
Frequently Asked Questions
Is the train still there?
Yes.
My GPS says to turn left on Broadway. Should I?
Your GPS is guessing. See Section One, then take Newhall.
I saw an F-35 downtown. Is that normal?
That was one time, and it got stuck behind the train like everybody else.
What's the best time of year to visit?
Locals say fall. The train says no comment.