When the weather is right, nothing beats enjoying a cold cocktail or beer outside on the patio of a great watering hole. Luckily Cherokee Street has some great options to do just that. Explore the patios in the district in the guide below and perhaps find a few you never even knew were there.

The Whiskey Ring — 2651 Cherokee

Go for: the largest patio on the street; the heated outdoor full bar on chilly nights

Opened in 2018 and expanded during the pandemic, the patio at Whiskey Ring is the largest on Cherokee Street, offering a full outdoor bar, several picnic benches and round tables, floor shuffleboard and a fire pit. Locals love the heated outdoor bar on chillier nights, as well as the cocktails and the whiskey selection. Soon, The Whiskey Ring will introduce a monthly outdoor concert series sponsored by local whiskey brand Withered Oak. The series is being produced in connection with the bar’s renown Western Wear Night, which began as “a group of friends dressing up like cowboys,” says owner John Joern. Little known fact: The Whiskey Ring was at one time the top-seller of Stag Beer in the world, and remains competitive to this day. 
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The Fortune Teller Bar — 2635 Cherokee

Go for: the hidden back patio and Gooseberries garden

Fortune says you would be remiss not to visit this time-tested bar and its hidden patio in the back. Fortune Teller Bar was the first of several Cherokee bars to open since a revival of the street’s nightlife began in the early 2010s. Not only can you enjoy a great cocktail and have your fortune read here, but the bar’s back patio is the hidden oasis you’ve been meaning to visit. Gooseberries, a local restaurant with its own brick-and-mortar location on Chippewa, runs the kitchen at Fortune Teller and maintains the herb and veggie garden in the bar’s back patio.

“Before the pandemic, our back patio was primarily a parking pad, but out of necessity and with a little bamboo fencing and a ton of plants, we transformed it into a little secret outdoor oasis,” said owner Matt Thenhaus.

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The B-Side at Night, Photo by Kevin Kelly

The B-Side —2709 Cherokee St

Go for: The divey vibe, burgers, late-night DJ sets, and small fire pit

Tucked away in the back, this gravel patio is small but worth mentioning, if only for its fire pit and the nightly party that exists beyond the door to the inside. Locals head to B-Side for the divey, neon red atmosphere, burgers, and frequent late-night dance parties featuring some of the city’s best DJs, all of whom are given the creative freedom to ditch the crowd pleasers and play what they want. “It’s an important spot for the music scene,” says Rory Flynn, aka DJ Makossa.

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Earthbound Beer — 2724 Cherokee

Go for: The multi-level patio, garden and walk-up window to order outside

The Earthbound patio is a great spot to catch food pop-ups during the warmer months, and of course, enjoy a variety of fresh beer from one of St. Louis’ most inspired breweries. Earthbound’s patio is multi-level, which means you can hang up top to watch the passersby and get some rays, or retreat to the level below for some privacy and shade. The patio also offers a walk-up window for those who want to limit their time indoors as much as possible.

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Yaqui's On Cherokee —2728 Cherokee

Go for: The pizza and wine, music seven nights a week, and summer curbside concerts

Yaquis is the neighborhood spot for pizza, wine and nightly free music. The bar and restaurant also offers a sidewalk patio that gets expanded into the street on Saturdays during the warmer months. From April through October, Yaquis puts on a curbside concert series every Saturday from 5:30 p.m. to 9:30 p.m.. Grab a table outside, order a glass of wine, a cocktail and/or some pizza, and enjoy some of the best local music in the area.

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San Loo – 3211 Cherokee

Go for: the punk rock dive vibe, outdoor live music and fire pit

A punk rock dive on the west end of Cherokee, San Loo totally renovated its back patio during the pandemic, adding an outdoor stage and tent, plus tables and a fire pit, for outdoor events and patio hangs. Locals head to the spot for the more than reasonable prices, the low-key, divey atmosphere, and regularly scheduled live music. Folk, Americana and punk rock take center stage when it comes to live music, but San Loo offers a variety and keeps things spontaneous.

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La Vallesana - 2801 Cherokee St

Go for: the excellent Mexican fare, margaritas and people watching

As we mentioned in our La Calle Cherokee Food Guide, La Vallesana has grown from a small ice cream shop into one of Calle Cherokee’s largest and most bustling restaurants, with a large outdoor patio. The patio is one of the best spots on Cherokee for drinks and people watching on a warm afternoon. Go ahead and get the margarita served in a big pineapple. It comes with two straws, but there’s no need to share. Also, don’t miss out on the quesadillas, tortas, tacos, and ice cream.

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