Lucky you. You just found KCtoday’s Plan Ahead, a list of some of the biggest events to plan for that are taking place throughout Kansas City each month.
Take out your calendar, grab your day planner, or text all your friends — these are the top events we recommend heading to this month. Psst: Don’t forget to bookmark this page and come back; we update our guide monthly.
(Don’t see anything you like? Check out our full events calendar.)
Festivals
¡Oktoberfiesta! | Wednesday, Oct. 1-Sunday, Oct. 12 | 12 p.m. | Boulevard Tours & Rec Center | Free | This Oktoberfest + Día de Los Muertos mash-up features 12 days of keepsake steins, an interactive ofrenda installation, limited-edition to-go crowler, German + Mexican-inspired food, and a limited release of Oak Aged Bob’s.
KC Blues & Jazz Fest | Friday, Oct. 3 | 3:30 p.m. | Legends Field, KCK | $56+ | Slide into the weekend with smooth jazz, gritty blues, and soul-shaking sets from local and national artists on multiple stages.
KC Oktoberfest 2025 | Friday, Oct. 3-Saturday, Oct. 4 | Times vary | Kansas City Bier Company | $17+ | With live polka, family fun, and German brews, it’s a biergarten blowout that drew 16,000+ last year.
PBR Outlaw Days | Friday, Oct. 3-Sunday, Oct. 5 | Times vary | T-Mobile Center | $47+ | Hold on tight — the world’s top bull riders hit the dirt for three nights of high-stakes, high-drama rodeo action.
Heartland Book Festival | Friday, Oct. 10-Saturday, Oct. 11 | Times vary | Multiple locations | Free with RSVP | From poetry slams to author talks, this two-day lit fest is a page-turner.
33rd Waldo Fall Fest | Saturday, Oct. 11 | 10 a.m.-6 p.m. | Waldo | Free |
This south KC fall tradition returns with food trucks like Neon Palm Ice, live performances, and kid-approved fun along Gregory Blvd.
Fall Fest | Saturday, Oct. 11 | 11 a.m.-5 p.m. | Zona Rosa North Park | Free | From seasonal fun like pumpkin decorating and fall-themed cocktails to in-store discounts and giveaways, this event is an autumn must in the Northland.
Family Fun Day by Kansas City Power & Light District and PNC Bank | Saturday, Oct. 18 | 10 a.m.-4 p.m. | Kansas City Power & Light District | Free | This event is replacing Cornucopia with a giant play zone featuring inflatables, games, crafts, and performances perfect for littles (and their grown-ups).
Weston Whiskey Fest | Saturday, Oct. 25 | 2-5 p.m. | Weston Burley House Inc, Weston | $60 | Sample whiskeys from around the world in a cozy fall setting, complete with cigars, in this historic riverside town.
Comedy
Caleb Hearon & Waxahatchee Present “Yeehaw!” | Thursday, Oct. 2 | 7 p.m. | Uptown Theater | $57+ | Local-ish comic Caleb Hearon teams up with indie darling Waxahatchee for a one-night variety show benefiting KC Tenants.
Henry Cho: “The Empty Nest Tour” | Friday, Oct. 10 | 8 p.m. | Uptown Theater | $51+ | With clean comedy + southern charm, Henry Cho’s got the dad humor down.
Fred Armisen | Friday, Oct. 17 | 6 p.m. | Arvest Bank Theatre at the Midland | $81 | The “SNL” and “Portlandia” alum brings his eccentric characters, musical bits, and dry-as-a-bone delivery to the KC stage.
Ben Schwartz & Friends | Friday, Oct. 24 | 7 p.m. | Arvest Bank Theatre at the Midland | $51+ | The improv king from Parks & Rec hits the stage with surprise guests for an unscripted night of chaotic hilarity.
Katt Williams | Saturday, Oct. 25 | 8 p.m. | T-Mobile Center | $100 | Expect no-holds-barred comedy and razor-sharp wit as the outspoken funnyman returns to KC on his “Heaven on Earth” tour.
Kauffman Center Presents “Whose Live Anyway?” | Wednesday, Oct. 29 | 7:30 p.m. | Helzberg Hall | $68+ | It’s 90 minutes of made-up-on-the-spot comedy from the cast of the beloved improv show.
Concerts + live performance
Jonas Brothers: “JONAS20 Greetings From Your Hometown” | Tuesday, Oct. 7 | 7:30 p.m. | T-Mobile Center | $51+ | The brothers are bringing a healthy dose of nostalgia to everything from “Burnin’ Up” to brand new bops.
Eternamente: A Día de los Muertos Spectacular | Friday, Oct. 10 | 7:30-10:30 p.m. | Midwest Trust Center, Overland Park, KS | $25+ | This show, an homage to Mexico’s rich cultural heritage, blends graceful traditional dance with vibrant storytelling that also tips a hat to the great Mexican singers of yesterday such as Vicente Fernandez, Pedro Infante, and Lucha Villa.
Kansas City Symphony Presents “Top Gun: Maverick” in Concert | Friday, Oct. 17-Sunday, Oct. 19 | Times vary | Helzberg Hall | $64+ | Buckle up for the ultimate adrenaline rush as “Top Gun: Maverick” takes flight on the big screen, with the Kansas City Symphony performing the electrifying score live.
Kansas City Ballet Presents “Swan Lake” | Friday, Oct. 17-Sunday, Oct. 26 | Times vary | Helzberg Hall | $34+ | Perhaps the most beloved ballet of all time, Swan Lake returns to captivate audiences with its iconic struggle of good versus evil set to the most lavishly romantic music ever written.
A Live Conversation with Freddie Prinze Jr. and Rachael Leigh Cook | Saturday, Oct. 18 | 7:30 p.m. | Midwest Trust Center, Overland Park, KS | $25+ | Step back into the late ‘90s for a special screening of “She’s All That,” followed by a live conversation with the film’s iconic stars, Freddie Prinze Jr. and Rachael Leigh Cook.
Playboi Carti: “Antagonist Tour” | Friday, Oct. 24 | 7 p.m. | T-Mobile Center | $57+ | Carti’s chaotic, bass-heavy tour hits KC.
SUGAR SKULL! A Día de Muertos Musical Adventure | Saturday, Oct. 25 | 11 a.m. | Starlight Theatre | $17 | This kid-friendly Día de Muertos musical mixes vibrant storytelling, catchy songs, and cultural celebration — all on KC’s favorite outdoor stage.
Tate McRae: “Miss Possessive Tour” | Tuesday, Oct. 28 | 7:30 p.m. | T-Mobile Center | $101+ | With viral dance moves and raw vocals, Tate’s live show is Gen Z pop perfection.
“Beauty & the Beast” | Tuesday, Oct. 28-Sunday, Nov. 2 | 8 a.m.-5 p.m. | Music Hall Kansas City | $52+ | Be our guest at Disney’s 30th anniversary production, with spectacular new sets and dazzling costumes from members of the original Tony Award-winning artistic team.
Kauffman Center Presents “PlayStation | The Concert” | Thursday, Oct. 30 | 7:30 p.m. | Kauffman Center | $54+ | Featuring the unforgettable music of “God of War,” “The Last of Us,” “Uncharted,” “Bloodborne,” and more, this show blends breathtaking musical performances with state-of-the-art visuals and immersive production.
Seasonal events
FrankenWines | Wednesday, Oct. 1 | 6:30 p.m. | Union Cemetery | $20 | Gather among the graves for a truly terrifying storytelling event. Each $20 ticket includes a sweet treat from McLain’s Bakery, as well as boozy and non-alcoholic libations.
Glow All Out | Friday, Oct. 3 | 6-11 p.m. | CPKC Stadium | $250 | NKC Health’s annual fundraiser goes aglow with diamond jewelry raffles, a glow-up accessory bar, drone show, and more — all meant to shine a light on critical patient care needs.
Merriam Drive Live | Saturday, Oct. 4 | 2-8 p.m. | Merriam Marketplace, Merriam, KS | Free | The suburb’s downtown transforms into a block party with two live music stages, food trucks, bevvies, and a cornhole tournament.
ArtSmash Kemper Museum Gala 2025: Riff/Evolve | Saturday, Oct. 4 | 7 p.m. | Kemper Museum of Contemporary Art | $350 | Style and music, emotion and technology, digital intimacy and analog simplicity — it all collides in this evening of drinks, dinner, and dancing.
Night/Shift: YES, AND | Thursday, Oct. 9 | 5 p.m. | The Nelson-Atkins Museum of Art | Free | Ditch the script and dive into a night of spontaneous creativity with a call-and-response musical mash-up, a stop-motion animation, puppet karaoke, and more.
Lenexa Chili Challenge | Friday, Oct. 10-Saturday, Oct. 11 | Times vary | Old Town Lenexa, Lenexa, KS | Free | With 200+ teams and endless samples, this spicy showdown is one of the region’s hottest fall traditions.
3rd Annual Westport Wine Walk | Saturday, Oct. 11 | 4-7 p.m. | Old Westport | $37 | Sip your way through twelve local haunts, including Char Bar, Holy Brunch, Laney’s Get Down, and Le Champion.
Brew at the Zoo | Saturday, Oct. 11 | 6:30-11 p.m. | Kansas City Zoo & Aquarium | $55+ | 30+ beers, animals after hours, and zero kids — it’s KC’s wildest beer fest.
Variety KC’s Heart & Swing | Monday, Oct. 27 | 8 a.m.-5 p.m. | Oakwood Country Club 9800 Grandview Road | $293 | Each drive makes a difference at this fundraiser tournament, featuring delicious food, cold drinks, and a lively atmosphere from tee-off to the final putt.
U.S. Women’s National Team v New Zealand | Wednesday, Oct. 29 | 7 p.m. | CPKC Stadium | $52+ | Catch the world champs take the field for an international friendly on our home turf.
Have an event of your own you want to share with us? Follow these easy steps to add your events to our calendar:
- Go to our Events page.
- Click “Add Event” in the top right-hand corner.
- Make sure to include a link and fill out important information like the date, time, location, and price of your event.
- Click “Submit,” and you’ve just added an event to our website calendar.