Osceola Music Series
Hot Music and Cool Rides!

Osceola Music Series
Osceola Music Series
Chestnut Street comes alive with the region’s hottest music series!  The Spring series kicks off Cinco de Mayo weekend May 3rd and each Friday through June 7th from 5:30pm to 9pm.  All shows are free and open to the public.  Everyone is encouraged to bring a cooler with the beverage of choice, food and snacks.  La Casita will be serving outside but this is also a BYO event if you don't want to purchase dinner at the restaurant. 

Live Music on the Square
Osceola Spring Music Series This year's Spring Music Series has new and returning acts from Kansas City, Versailles, Iconium and El Dorado!  We kick things off with the Dave Stubblefield Band, a great 4-piece band from the Warsaw area on May 3rd as we celebrate Cinco de Mayo with dinner and drink specials at La Casita.

Cruise Night
New for 2024 we will feature a Cruise Night on the Osceola Square!  If you've got a ride, bring it out and enjoy the live music on the Osceola Square!  Cars will be parked on Chestnut Street just down from the music.  Join fellow car enthusiasts, share some conversation, enjoy some good food from La Casita and see some great cars!  Registration is free!

PARKING OPENS AT 4:30PM
FREE ADMISSION. NO REGISTRATION REQUIRED. LIMITED SPACES SO PARKING IS ON FIRST COME FIRST SERVE BASIS.

Osceola Spring Music Series

BYO Event
La Casita will once again be serving guests outside to enjoy the music or enjoy dinner inside the restaurant.  This is a BYO Event meaning you don't have to eat at the restaurant to enjoy the music!  Bring a cooler and food or snacks and enjoy the music on the square.  Bring a lawn chair and enjoy this free event at any of the shows from the first show on May to OH CRAP in October!

Osceola Spring Music Series

Fall Music Series
The Fall Music Series will kickoff with the Annual Osceola Street Dance on Thursday August 29th on the Square with The County Liners playing from 5pm to 9pm!  The Osceola Senior Class will be serving their Famous Chicken Dinner and the Osceola Optimist will be serving Hamburgers, Hot Dogs, sodas and water.  La Casita will be serving Street Tacos and regular and frozen margaritas!  Become a "Street Vendor" at this years Street Dance: Street Dance Vendor Form.

Pay attention to Fall Music Series dates as the Street Dance and OH CRAP are not on the usual Friday nights!

Osceola spring Music Series

OH CRAP
The Osage Hills Connection Route After Party (OH CRAP) will feature live music on the square and a day of fun cheering arriving bike riders from Clinton, Bolivar and points in between to Osceola.  The Osage Hills Connection Route is a route that connects the Frisco Trail in Bolivar to the Katy Trail in Clinton, October 5th is our 3rd Annual Ride!  For some Osceola will be the mid-point, for others Osceola will serve as the end point.  All will enjoy the sights, sounds and food of Osceola!  Part of the Chamber's Fall Music Series this will feature an afternoon show with live music from Randy Polson on the Osceola Square from 11am to 2pm!

Music Series Sponsors














 
Osceola Music Series

2024 Spring Music Series Lineup
SPRING MUSIC KICKOFF!
Friday
May 3, 2024
5:30pm - 9pm
  Osceola Music SeriesCinco De Mayo Weekend
DAVE STUBBLEFIELD BAND

WARSAW AREA
Country

Friday
May 10, 2024
5:30pm - 9pm
  PONCH BURKHART
VERSAILLES MO
Country, Rock

Friday
May 17, 2024
5:30pm - 8:30pm
  GARRY LINCOLN MUSIC
KANSAS CITY MO
Country

Friday
May 24, 2024
5:30pm - 9pm
  RANDY POLSON
THE CAMPFIRE COWBOY

ICONIUM MO
Country

Friday
May 31, 2024
5:30pm - 9pm
LONESOME EAGLE BAND
ROSCOE MO
Country

Friday
June 7, 2024
5:30pm - 9pm
  SUMMER KICKOFF!
THE COUNTY LINERS
POLK, ST. CLAIR COUNTY
Country

 
 

2024 Fall Music Series Lineup
Street Dance
Thursday
August 29, 2024
5pm - 9pm
  RODEO DAZE KICKOFF!
THE COUNTY LINERS
POLK, ST. CLAIR COUNTY
Country
Become a "Street Vendor": Street Dance Vendor Form
Osceola Music Series  Osceola Music Series  Osceola Music Series

Friday
September 6, 2024
5pm - 8pm
  To Be Announced

Friday
September 13, 2024
5pm - 8pm
  To Be Announced

Friday
September 20, 2024
5pm - 8pm
  PONCH BURKHART
VERSAILLES MO
Country, Rock

Friday
September 27, 2024
5pm - 8pm
  To Be Announced

Saturday
October 5 2024
11am - 2pm
OH CRAP
Osage Hills Connection Route After Party

Osceola Music SeriesRANDY POLSON
THE CAMPFIRE COWBOY

ICONIUM MO
Country
    Osceola Music Series Osceola Music Series Osceola Music Series

Osceola Music Series Osceola Music Series
Osceola Lodging
Spend the Night in Osceola for This Event!
Osceola has two Airbnb locations right on the downtown square!  All the rooms are newly renovated and locally owned and operated!  Both locations are within walking distance of dining, shops, funeral home and most downtown events.  Stay in the heart of Osceola!  Our rooms welcome you!


The Historic Commercial Hotel
Osceola Music SeriesThe Historic Commercial Hotel (Est.1868) on the Downtown square in beautiful Osceola, Missouri. Old world feel with modernized accommodations. The Historic Commercial Hotel has numerous themed rooms which are designed and named after past historical guests.

Check Available Dates:
Sally Rand Suite - 2 guests 1 bedroom 1 bed 1 private bath
Tom Mix Suite - 4 guests 1 bedroom 2 beds 1 private bath
The Dam Room - 3 guests 1 bedroom 1 bed 1.5 shared baths
Lone Wolf Room - 2 guests 1 bedroom 1 bed 1.5 baths
The Quiet Room - 2 guests 1 bedroom1 bed 1.5 shared baths



The Chestnut on the Square
Osceola Music SeriesThe Chestnut on the Square offers one and two bedroom apartments! Newly renovated 2nd floor with Loft A includes 2 bedroom 2 bath loft with kitchen, dining area and large living space with floor to ceiling windows overlooking the square!

Check Available Dates:
Historic Loft A - 4 guests 2 bedrooms 3 beds 2 baths
Historic Loft B - 3 guests 1 bedroom 2 beds 1 bath

Osceola Camping & RV  
Arrowhead Point RV Park, Cabins & Campground
Osceola Music SeriesLocated just 16 miles from the Osceola Square is Arrowhead Point.  You'll find over 40 acres to hike and explore, a catch-and-release fishing pond, and plenty of room to kickback around a campfire with friends and family.  Amenities include water, sewer, trash, electricity, and Wi-Fi.  There are 5 cabins varying in size and accommodations as well as 40 pull-through, full hook-up sites to choose from in a mix of shade and sun, there's a perfect spot for everyone!
Web Site
Book Your Stay

Getaway House
Osceola Music SeriesLocated just 8.5 miles from the Osceola Square is Getaway Ozarks Highlands.  Tiny cabins nestled in nature, our outpost offers multiple walking trails to immerse yourself in nature.  Cabins are nestled along a ridge, providing lush hill and forest views of majestic hardwood trees that change with the season.  Our Outposts are designed to be more than a destination, but a way to create distance from the relentless demands of work, schedules, and technology.  We want our guests to experience unscheduled, unstructured, and uninterrupted free time — not just for rest and rejuvenation, but to foster inspiration, creativity, and connection.
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Book Your Stay

Osceola Music Series