Baraboo, WI: A Circus Town with Schitt’s Creek Charm & Delicious Pizza

State mask, vaccine, and travel mandates are updating often – please double check state and local guidelines to keep yourself and others safe. Also double check what’s open before your trip.

Living in Wisconsin has had its ups and down… from weekly, wonderful and fresh Farmers Markets during the summer in Madison, to weather with a “real feel” of near 25 degrees below zero last winter. But it also has its specialness like my hometown in Westchester County, NY — from its awesome, spot-on Fall foliage and activities, to its equally-charming surrounding small(er) towns.

The BF got a new car and wanted to really “drive it” since we don’t drive very far during the week to work. We decided to visit a neighboring town called Baraboo, about a 45-min drive from Madison’s far West side. Sound circus-like?

If you said “yes, it sounds circus like”, then you’re right(!) because the city was the home of the Ringling Brothers from 1884 to 1917 which has since lead to its nickname, “Circus City”.


I have a co-worker who I pinged for ideas on a quick tour-de-Baraboo and, while it is a small town, I did find a couple gems that I just had to share.

First and foremost… y’all know I live for pizza. One of the top recos from my co-worker was eating at a place called “Gem City“. Upon Googling, it looked like a definite Cheers/small-town bar… “AMAZING pan style pizza”? I was doubtful.


Dudes… the pan-style pizza was AMAZING. Below is a beautiful still life of the “small” Gem City Deluxe and it was simply divine. Paired with some of the coldest tap beer I’ve had in a while, and this 45-min drive was worth it off the bat.


You’re likely wondering why the Schitt’s Creek reference?

Well… I’ll start by sharing that it’s truly one of my favorite shows ever. Do yourself the favor and watch at least 4-5 episodes of the 1st season and you’ll understand why I’m not the only one that thinks it’s one of the best shows ever, and why I’ve referenced it in this post.

Assuming you know a little context (rich family moves to a podunk town called Schitt’s Creek – it’s all they own and, therefore, the only place they have to live), as we sat at Gem City Saloon & Eatery, the only view was of what felt like an area of town that really had charm and character at one point in history but has needed some love since; similar to the “love” David Rose gives to Schitt’s Creek over the course of the show.

I couldn’t help but think: that building across the street could be SUCH a “Rose Apothecary” in this little town; or a “Lucille” like we have in Madison (a great restaurant in a restored bank). The one open building/storefront diagonal from Gem City was this thrift and variety shop which turns out used to be an ice storage building and had a pretty cool, enormous vintage door inside.

Of course, we didn’t leave this Family Values spot without some “vintage” finds: 2 CDs (The Brady Bunch and Dave Matthews Band) and a Pleasant Rowland – Learning Company (now American Girl) mint-condition tin container.


Last but not least, we took a quick walk through downtown (3-4ish main streets). Super cute, storefront after storefront leading right up to a Ringling Bros mecca, the Al. Ringling theatre, built by Al. Ringling to “show up” his brother but also…

“The Al. Ringling Theatre in particular, built as a gift to Baraboo, stands as a testimony to his affection to his adopted hometown.  The name of Ringling will always remain a cornerstone of the cultural heritage of this unique Midwestern city.


Sadly, I did not visit Circus World, another cornerstone of the town and Ringling Bros legacy, but I know I’ll be back not just for that delicious Gem City pizza and cold tap beer but also because the town sits in a bit of a valley and… can we say Fall foliage? Yas.

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