Despite the absence of a master plan, this former no-man's-land has flourished organically, cultivated by young entrepreneurs. Start on "Antique Row," a stream of thrift shops dotted with neighborhood cafes. Walk west and the vibe gets more artsy, with progressive galleries, boutiques, and the highest concentration of Mexican restaurants in the city.
"Cherokee Street is to St. Louis what St. Louis is to the rest of the country," says shop owner Randy Vines. "It's often overlooked, but anyone who takes the time to explore it will find how special and vibrant it is."
Here's nine of our favorite spots along the up-and-coming street:
1. Siete Luminarias For years, it was the heavy concentration of Mexican restaurants that drew traffic to Cherokee. The latest addition is the kitschy-but-delicious Siete Luminarias. Get the pambazo ($9), a street-food staple rarely found north of the Rio Grande.
2. The Fortune Teller Bar A throwback to the space's previous life as a dive bar run by a tarot reader, the menu honor the owners' German roots with dark lagers on tap and cocktails such as the Ein Grüne Hut ($8) capped with dill from the garden.
3. Scarlett Garnet In 2012, the owners behind edgy jewelry line Scarlett Garnet opened a storefront where you can shop from the labels' newest baubles, as well as hand-sewn tops and colorful accessories from other Missouri designers.
4. STL-Style Twin brothers Jeff and Randy Vines opened their shop in 2009 as a source for screen-printed shirts and accessories that rep the city they know and love. Slogans such as "You Can't Spell Style Without STL," and "Get Your Thrills in St. Louis Hills" make these T-shirts ($22.95) and posters ($32.95) much cooler than your average souvenir. If you find a design you love, but not the color, have a T-shirt custom-made on the spot.
5. Whisk Bakeshop In the midst of antiques shops that make up the eastern strip of Cherokee, this year-old sustainable bakery promises every pop tartlet, cupcake, and bacon-chocolate-chip cookie is baked fresh daily using local ingredients. "I grew up two neighborhoods away from here," says owner Kaylen Wissinger." It's great to be a part of the renaissance and be surrounded by so many young, creative people to bounce ideas off."
6. Retro 101 Follow the cool kids, including frequent shopper and local musician Pokey LaFarge, to this vintage shop where you can find anything from pocket squares for under $10 to $25 1950s house dresses and a 1920s beaded chiffon frock for $450. An institution in the area for more than 10 years, Retro 101 is the first stop for those looking for one-of-a-kind furniture, clothes, and knickknacks. 314/762-9722
7. Foam Coffee & Beer This is where hipsters young and old converge at the end of the day to scope the lineup of emerging indie talent the bar is known for booking. You'll fit in by ordering a PBR and pretzel croissant ($4). For an added kick, go for a Kosmonaut ($6), Foam's version of a White Russian.
8. Junk Junkie When mid-century modern furniture shop MoModerne moved off Cherokee and into the suburbs, owner Luby Kelley kept the space and turned it into a resale home store that offers the same level of taste and quality, but at a much lower price point. 315/495-4095
9. Art Galleries The shift in Cherokee began when galleries started to move in during the early 2000s. Fort Gondo led the way with its ever-changing collections, exhibitions, poetry readings, and community events. Newer ventures such as Blank Space (2847 Cherokee Street) are more like collectives, where you can encounter anything from a craft sale to an electronic music show. This year, The Luminary, credited with bringing indie names such as Athens rock band of Montreal and mixed-media artist Gabriel Dawe to the area, moves into a 16,000-square-foot space, raising the ante on Cherokee's art scene by adding shared resources for creatives.
Did we miss anything? Tell us your favorite spot on St. Louis' Cherokee Street in the comments below.