The Best Things To Do in St. Louis During the Weekend, September 23 to September 25

Check out Taste of St. Louis, Oktoberfest, Tower Grove Pride and much more

click to enlarge A woman smiles as she's about to take a bite of food at Taste of St. Louis.
Taste of St. Louis will feature around 30 local food vendors.

This might be the most hopping weekend of the year to date in the greater St. Louis region. If leather contests aren't your thing, hop onto Shakespeare, Tower Grove Pride, walking tours of the city's hot spots or the Greater St. Louis Hispanic Festival.

Don't forget to plan your week while you're at it!

Friday 09/23

Leather Daddy

The longest-running annual leather contest in the country sponsored by a single leather club is back for its 39th year. Mr. Missouri Leather Weekend 2022 kicks off with the Black and Lou Fetish Ball on Friday, September 23. Show up late to the ball, and you may be punished, organizers say. During the day on Saturday, September 24, you can enjoy Master Kink Klasses, educational seminars open to the public. The pageant itself will begin at 10 p.m. that day. Contestants will be judged on cruise wear, physique and personality, formal wear and a short speech. Admission is $10. Finally on Sunday, September 25, join the Mr. Missouri Leather Victory Brunch at 12:30 p.m. Cost is $30 and includes two drinks and brunch. All events are at Tropical Liqueurs (4104 Manchester Avenue, 314-899-9404), except the official after party, which will be at Rehab Bar and Grill (4054 Chouteau Avenue, 314-652-3700) on Saturday.

click to enlarge Two Mr. Missouri Leather contestants stand on stage.
Scott Layne
Mr. Missouri Leather is the longest running annual leather contest in the country.

Tilting at the Windmill

Dust off your finest lederhosen and start exercising your stein-hoisting arm because Das Bevo's (4749 Gravis Avenue, 314-832-2251) second annual Oktoberfest celebration is upon us. The festivities kick off Friday night with an accordion-led performance by Larry Hallar's Good Times Band and continue all weekend long. Bring the kids and let them pogo to the polka in the bounce house; bring your long stubby pups for a chance to take home the gold in the weiner dog costume contest; and definitely bring a designated driver so that you may properly quench your thirst. There will be plenty of live music and party vibes, and perhaps best of all, the whole event is free. We'll prost to that! For more information, visit


It's uncommon for a humorous novel to win the Pulitzer Prize, and it's not every day a Pulitzer Prize–winning novelist comes to town. So don't miss the opportunity to see Andrew Sean Greer read from his new book and take questions at the beautiful Ethical Society of St. Louis (9001 Clayton Road, Ladue; 314-991-0955). Greer's very funny novel Less is about a middling novelist, Arthur Less, who needs to get out of town to escape a dreaded wedding invite. So he goes on a round-the-world literary tour. It won the Pulitzer in 2018. Now Greer is back with Less is Lost. Same character. Different adventure. The event kicks off at 7 p.m. and costs $34 for one or $39 for two.

Saturday 09/24

click to enlarge Pride in Tower Grove. - Alexis Hitt / RFT slideshow
Alexis Hitt / RFT slideshow
Pride in Tower Grove.

Pride in the Park

Tower Grove Pride used to be one of the best (and hottest) parties of the year. The outdoor celebration of all things queer used to happen during Pride Month in June, which meant that many people spent their weekends in Tower Grove Park sweating off their rainbow eyeshadow. But many things changed with the pandemic, including the scheduling of this big party. Because of a huge wave of COVID-19 cases, it was pushed until September last year, and well, everybody loved it. Cooler temperatures (and a bit of a breeze) helped to raise the vibe even higher, so the organizers stuck with it. This year at Tower Grove Pride, you can find all of the same features you enjoy each year like music, food, shopping and an endless amount of opportunities to volunteer to help the community. The event begins at noon, and admission is free. Visit for more information.

Viva St. Louis

Somewhat confusingly, Hispanic Heritage Month — the U.S. commemoration of the contributions of Hispanic and Latinx peoples — began on September 15 and runs until midway through October (the month roughly begins with Mexican Independence and ends around Día de la Raza). In the metro area, there's perhaps no better way to celebrate than to attend the Greater St. Louis Hispanic Festival, which kicks off at Soulard Park at 10 a.m. Saturday, September 24, and ends on Sunday, September 25, at 8 p.m. This year's festival returns after a two-year hiatus with live music from national artists; the food of Mexico, Colombia, Honduras and more from local vendors; folkloric dancers from Carnaval de Tlaxcala; craft vendors from Bolivia, Mexico and Ecuador; a los niños corner for the kiddos and more. The organizers welcome St. Louisans of all ethnicities, and admission is free.

Shakespeare at the Mill

click to enlarge Flyer for Shakespeare in the Streets
Courtesy Shakespeare St. Louis
Take in an unconventional performance this weekend.

If you're strolling through the heart of Bevo Mill this weekend, you might catch an unusual sight: a full-on Shakespeare production. But Shakespeare in the Streets isn't a regular-old staging but rather an original play that's created from stories from residents in a specific neighborhood as well as an existing Shakespeare work. In Bevo Mill, this includes highlighting the rich history of immigrants in the neighborhood and its roots in Germany, Bosnia and Afghanistan. It will be the ninth Shakespeare in the Streets production yet –– all taking place in different St. Louis neighborhoods, stretching from the Ville to Maplewood, and now to Bevo Mill. The event, which starts at 8 p.m., is free. Show up early to grab a lawn chair or bring a blanket or your own chair, and enjoy the show. For more information, visit

Jewel Box
Photo courtesy of Flickr / CWMc
Take a walking tour of the Jewel Box this weekend.

Walk This Way

After highlighting the best of San Francisco; Boston; and Washington, D.C., the Cultural Landscape Foundation turns its attention to St. Louis and the Missouri River Valley this weekend — with a roster of free walking tours Saturday and Sunday designed to introduce locals and visitors alike to the great public sites dotting the region. What's Out There Weekend St. Louis includes an architect-led tour of Forest Park's Jewel Box, a docent-led tour of downtown Hermann, a preservationists' take on Greenwood Cemetery and much, much more. There are no less than 35 illuminating options, with the chance to spend 60 to 90 minutes appreciating spots from Carondelet Park to the city's Ville neighborhood to Fort Bellefontaine. The goal? To help you discover the little-known design history of places you pass by every day. Visit to see the rundown and register. All of the tours are free.

Sunday 09/25

Art Outdoors

Seeing art in St. Louis' fine galleries and museums is hard to beat. But going to an outdoor art event where you can pick up some great pieces to take home and admire 24/7 might be even better. One of the finest such opportunities to do so comes at Art in the Park St. Louis Hills. The family-friendly fest returns this year after a two-year hiatus. Visitors will be able to enjoy art, music and food against the beautiful backdrop of Francis Park (intersection of Eichelberger Street and Donovan Avenue) and its lily-festooned pond. Visitors can opt into the festival's $1 raffle, which has prizes that range from jewelry to prints to sculptures and wall art. The festivities kick off at 10 a.m. and run through 5 p.m. Admission is free. More information at

St. Louis Smorgasbord

Calling the ambitious, the indecisive, the adventurous — the eaters of St. Louis. This weekend is your weekend because it's Taste of St. Louis at Ballpark Village (601 Clark Avenue). The event, which bills itself as "St. Louis' biggest free event," brings together about 30 local food establishments every year to create what's certainly the city's biggest smorgasbord. This year's lineup is too long to share here but features an eclectic mix including Simba Ugandan Restaurant, Hi-Pointe Drive-In and Boardwalk Waffles & Ice Cream. There will also be live music throughout the weekend: Ozomatli on Friday, September 23; Eli Young Band on Saturday, September 24; and James Biko and DJ Dune with Keys Bass & Drums to finish things off on Sunday, September 25. Admission is free, but food costs vary. Hours daily.

Have an event you'd like considered for our calendar? Email [email protected]

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