Osceola Music Series Hot Music and Cool Rides! 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 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. 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! 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   Cinco 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     Friday September 6, 2024 5pm - 8pm   To Be Announced Friday September 13, 2024 5pm - 8pm   To Be Announced Friday September 20, 2024 5pm - 8pm   To Be Announced Friday September 27, 2024 5pm - 8pm   To Be Announced Saturday October 5 2024 11am - 2pm OH CRAP Osage Hills Connection Route After Party RANDY POLSON THE CAMPFIRE COWBOY ICONIUM MO Country     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 The 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 The 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 Located 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 Located 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. Web Site Book Your Stay