Osceola Music Series Fall Music Series Osceola Fall Music Series Our Fall Music Series has some new acts from Warsaw and Quincy as well as some returning popular acts!  We kick things off with the Annual Osceola Street Dance on August 31 and end on Saturday October 7th with OH CRAP the Osage Hills Connection Route After Party!  Pay attention to dates as the Street Dance and OH CRAP are not on the usual Friday nights! Street Dance Kickoff The Annual Osceola Street Dance will be on Thursday 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!  A first this year will be the Stick Horse Race presented by Bray & Company Real Estate where young riders will run a barrel style race!  Always a great time, come out and support these local organizations! Fridays in September Our Friday Music Series begins on September 8th and runs each Friday in September from 5pm to 8pm.  Just like the Spring Series the 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. 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 7th is our 2nd 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! BYO Event La Casita will once again be setup with outside seating and serving guests outside to enjoy the music or eat inside.  This is a BYO Event meaning you don't have to eat at the restaurant.  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 street Dance to OH CRAP! Music Lineup FALL MUSIC KICKOFF! Thursday August 31, 2023 5pm - 9pm   Osceola Street Dance THE COUNTY LINERS ST. CLAIR, POLK, HENRY COUNTIES Country September 8 5pm - 8pm   JEFF CAUDLE QUINCY MO Country, Pop, Rock September 15 5pm - 8pm   RANDY POLSON THE CAMPFIRE COWBOY ICONIUM MO Country Sac Osage Publishing Night! Look for a La Casita coupon in the September 20th Buyers Guide September 22 5pm - 8pm COLT-n-RACHEL WARSAW MO Country, Pop, Rock September 29 5pm - 8pm   JIM & DARLENE HAYES WARSAW MO Country, Bluegrass, Gospel October 7 11am - 2pm   OH CRAP Osage Hills Connection Route After Party RANDY POLSON THE CAMPFIRE COWBOY ICONIUM MO Country       Osceola Lodging   Stay the Night! Spend the night in Osceola for this event!  Osceola has two Airbnb locations and 7 rooms right on the downtown square!  All the rooms are newly renovated and locally owned and operated!  Both locations are within walking distance of the music and shops you'll discover on Saturday Morning!  Make it a full evening and stay the night in Downtown Osceola and Explore Osceola on Saturday!  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 Music Series Sponsors