Osage Hills Connection Ride
Connecting the Frisco & Katy Trail

Osceola Chamber Luncheon
3rd Annual Ride
Our 3rd 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 3rd 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!

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 5th in Clinton and Bolivar, T-Shirts & swag bag pickup will be 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!

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Download FIT File

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

After your ride the party begins!  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 on the Osceola Square from 11am to 2pm!

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





Randy Polson
October 7, 2023

Randy Polson
October 7, 2023

Randy Polson
October 7, 2023

Map of Route


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Nav Files

GPX File

FIT File

OHCR Sponsors









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!
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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.
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