Osage Hills Connection Ride Connecting the Frisco & Katy Trail 2nd Annual Ride Our 2nd Annual ride features a new route with less gravel and a great scenic ride connecting the Frisco and Katy Trails!  The scenery in October will be at it's peak and you will enjoy a great ride through this rural area just waiting to be explored!   Riders can start in either Bolivar, Clinton or points along the way for a ride that fits your expertise!  Osceola, about half way, will host an After Party (for some it will just be half way) on the Osceola Square that will commemorate the 2nd Annual Ride with music and food from 11am to 3pm.  La Casita Mexican Restaurant will be serving food on the square (weather permitting) and inside the restaurant. A Ride for Everyone What makes this ride unique is there are several start options depending on your expertise!  Not up for the full 86.2 miles?  Start somewhere in between and end in Osceola for a shorter ride!  Start in Humansville and ride to Osceola for a total of 21.7 miles!  Looking for something longer?  Bolivar-to-Clinton-to-Bolivar will give you a 172.4 mile ride with overnight accommodations available in Clinton, Osceola and Bolivar.  Start in Clinton, Bolivar or points in between and end in Osceola or continue on, it's your ride! Signup Here 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 riders from Clinton, Bolivar and points in between to Osceola.  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 Lineup October 7 11am - 2pm   OH CRAP Osage Hills Connection Route After Party RANDY POLSON THE CAMPFIRE COWBOY ICONIUM MO Country About This Ride This route was developed by some dedicated riders to connect the Frisco Trail in Bolivar to the Katy Trail in Clinton.  This has turned into a project involving 3-counties and a multi-city area working together to promote biking and this route in Southwest Missouri and beyond!  This ride was developed to promote the route, get riders and their feedback and eventually get permanent signs installed along the route.  All proceeds from this ride are going to be used to promote the route and get signage installed!  By participating in or sponsoring the ride you are bringing your support to this project! Day of Ride Registration on starts at 8am on October 7th in Clinton and Bolivar, T-Shirts & swag bag pickup will be in Osceola in Osceola.  Shirt Cutoff will be September 20th. The Osage Hills Connection Route Check out the route map with surfaces, Cuesheet and elevation here.  Located in the beautiful Ozarks with October scenery that will be at its peak for a great ride through this rural area just waiting to be explored! Download GPX File Download FIT File Signup Here Route Options Riders have several ride options depending on their experience. Bolivar to Humansville - 20.1 Miles Humansville to Osceola - 21.7 Miles Bolivar to Osceola - 41.8 Miles Bolivar to Clinton - 86.2 Miles Clinton to Osceola - 44.4 Miles Clinton to Bolivar - 86.2 Miles Bolivar to Clinton to Bolivar - 172.4 Miles Signup Here Map of Route Elevation 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 Online Signup Signup Here Nav Files GPX File FIT File OHCR Sponsors