Tour de Cherokee Street

 In Feature, Food

The eclectic streets watering holes feature dive bars, whiskey joints and cocktails aplenty.


One happy place where I always steer both uninitiated locals and curious out-of-towners is Cherokee Street. Cutting east to west through Benton Park, it’s populated with all manner of eclectic retail, cultural and culinary destinations. Some have been doing business for years; others are relatively new kids on the block, but this vibrant stretch of road has undergone a long-overdue renaissance in recent years. As a result, the neighborhood has seen a boom in bar openings west of Jefferson Avenue.

One thing I love about this area is that I can park and go about my business on foot. There’s a sign in the window of one of the buildings here that says “Walk Your Neighborhood,” and that’s good advice—Cherokee needs to be experienced at ground level. Thankfully, Cherokee hasn’t succumbed to bland gentrification and chain store banality. Instead, the area has been invested in by folks who wish to remain independent and go their own way, which is at the very heart of the neighborhood’s character. Sure, there are some (to paraphrase Anthony Bourdain) “sock-head hipsters” and faux-hippies twirling about, but by and large, this street is about solid, salt-ofthe-earth folks who are less interested in trends than putting out quality food and drinks in a convivial atmosphere.

Of course, to get the Cherokee experience you have to experience the people and places for yourself. Here’s a recap of my last excursion to give you some inspiration:


There are plenty of spirits and beers on the list here, and they also have a pretty extensive food menu ranging from snacks to sammiches, so come hungry. Make sure to set your fork down to play with the Magic 8 Ball and admire the fine examples of taxidermy gazing down upon you. And definitely try a house cocktail. On this visit I indulged in the My Milk Stout Brings All The Boys To The Yard: a mix of 4 Hands Chocolate Milk Stout, Thunderbest Baby Buffalo Bourbon, orange bitters and a house-made chili pepper syrup (the title is bigger than the drink), and discussed the dangers of riding a scooter in South City with Dave the bartender (2635 Cherokee St.).


This joint specializes in (wait for it)…whiskey. And they have a pretty fine array in their collection, which occasionally includes hard-to-get bottles like W.L. Weller 12. They make a mean cocktail with all of those delicious brown liquors as well. This time around, I enjoyed a nip of Rittenhouse Rye while taking in the impressive collection of velvet paintings that adorn the walls—Stallone as Cobra is my personal fave—and eavesdropped on a spirited debate between two flannel-clad lads at the end of the bar about the relative merits of PBR vs. Stag. Consensus: both are cheap and pretty good but better when paired with equally cheap and good whiskey (2651 Cherokee St.).


This is always a priority stop because co-owner Tom Halaska and crew never fail to make me feel like a regular, even when I haven’t been around in a while. Unfortunately, there was no burlesque performance happening during my latest visit, so I made due with a Negroni, a coloring book and some crayons. In addition to cocktails, beer and spirits, there’s grub to be had here as well—and not just bar food. Sausage crepe, anyone? P.S. The crazy mosaic floor here alone is worth the visit (2732 Cherokee St.).


Now this is what I call a true dive bar—in the best sense. If you don’t feel immediately at home here, you’re probably not living right. Just a bar, some booths and a kick-ass digital jukebox—do you really need anything else? This time around, I downed a couple of well bourbons, chowed on a Companion pretzel with some horseradish and listened to Bad Company while rhapsodizing about Brooklyn with a heavily tattooed artist and her dog. The dog didn’t have much to say (3227 Cherokee St.). Let’s be honest: I only scratched the surface on this trip. You could probably spend a month on Cherokee and not experience all the goodness that abounds. So get up, get moving and experience the Tour de Cherokee and see for yourself.




Photo credit: Illustration by Noah MacMillan

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