Windsor, MO

Windsor sits in Henry and Pettis counties, a city laid out in 1855 as Belmont and renamed in 1859 for Windsor Castle. The 2020 census counted 2,775 residents. The old wagon route became Main Street, and later railroads turned the crossroads into a shipping town for brooms, buttons, chickens, cheese, and other local goods. Today, Missouri Routes 52 and 2 meet the broader highway network here.

The trail connection is Windsor’s big local surprise. The Katy Trail and Rock Island Spur meet at the town, making Windsor the only point where the two routes connect. Farrington Park sits near the trails and its lake, so the rail history has a modern foot-and-bike version now. Windsor still has the county-road feel of west-central Missouri - a grid of streets, a Main Street shaped by old travel, and a trail junction that brings a second kind of traffic through town. The Henry County R-1 schools keep the town’s daily calendar rooted here.