𝟑𝐫𝐝 𝐀𝐧𝐧𝐮𝐚𝐥 𝐎𝐬𝐚𝐠𝐞 𝐇𝐢𝐥𝐥𝐬 𝐂𝐨𝐧𝐧𝐞𝐜𝐭𝐢𝐨𝐧 𝐑𝐢𝐝𝐞

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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 11 a.m. to 3 p.m. 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 three 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 5 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 23 for processing and printing
Online Registration cutoff: October 4 @ 11:59 p.m.
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 11 a.m. to 2 p.m.!
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.


Bolivar, Clinton, Osceola
1710 W. Broadway St.
Bolivar, MO 65613

Additional Information

Travelers With Disabilities Information
No Accommodations
Smoking Policy
Smoking Allowed Outdoors Only
Cost Of Admission
Charges Admission
Pet Policy
Pets Allowed Outdoors On A Leash
Service Animals Welcome