Skip to main content

3rd Annual Osage Hills Connection Ride

Sat October 5, 2024 Osceola, MO 64776 US Directions


3rd Annual Osage Hills Connection Route Ride - Bolivar Start

$30 8:00AM CDT Registration ends October 4, 2024 at 11:59pm CDT

3rd Annual Osage Hills Connection Route Ride - Clinton Start

$30 8:00AM CDT Registration ends October 4, 2024 at 11:59pm CDT

Race Website

Additional race information can be found at


780 2nd St
Osceola, MO US 64776


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.

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 provide biking and this route in Southwest Missouri and beyond!  This ride was developed to promote the route, get rider 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 or sponsoring the ride you are brining your support to this project!

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!

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.

Dates To Remember:
T-shirt Cutoff - September 23rd for processing and printing
Online Registration cutoff: October 4th @ 11:59pm

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!

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 - 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

NOTE: You do not need to do the full route if you do not wish. It is up to you to find a ride back to your starting point.

Race Contact Info

If you have any questions about this race, click the button below.



If you continue to use this site, you consent to use all cookies. We use cookies to offer you a better browsing experience. Read how we use cookies and how you can control them by visiting our Privacy Policy.

If you continue to use this site, you consent to use all cookies.