Osage Hills Connection Route Connecting the Frisco & Katy Trail 2nd Annual Ride Come out and participate in the 2nd Annual ride for the Osage Hills Connection Route! This route connects the Frisco Trail in Bolivar Missouri to the Katy Trail in Clinton Missouri. Riders can start in either Bolivar or Clinton with Food and Music along the way. Osceola Missouri will host an event on the square that will commemorate the inaugural ride with music and food from 11am to 3pm. Registration starts at 8.. Find The Route Find the route map with surfaces, Cuesheet and elevation online here. Route Options Riders have several ride options depending on their ability. Bolivar to Humansville - 22.5 Miles Bolivar to Osceola - 44.5 Miles Bolivar to Clinton - 79.8 Miles Clinton to Osceola - 35.3 Miles Clinton to Bolivar - 79.8 Miles Map of Route 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