Every year on Labor Day weekend, the community of Windsor comes together to celebrate everything it means to be a small town in the Midwest! Windsor is centrally located in a peaceful rural community, a short drive from the larger communities of Sedalia, Clinton, and Warrensburg.

Enjoying close proximity to Whiteman Air Force Base and the beautiful Lake of the Ozarks, Windsor lies at the intersection of Henry, Johnson, Benton and Pettis counties. Windsor enthusiastically celebrated its 150th Birthday in 2005. The Sesquicentennial was a huge success and we felt this just had to continue on.

Schedule Of events

Aug 24,2025

2pm - Wee Queen and Wee King Judging Windsor United Methodist Church

4pm - Miss Windsor Judging Windsor United Methodist Church

Aug 28,2025

5pm - Dinosaur Take Over Show
Free, Former Umb Bank Parking Lot

5-10pm - Carnival

6pm - Dinosaur Take Over Show

6:30pm - Wee Queen and King Crowning
Septemberfest Main Stage Rain Location Windsor United Methodist Church

7pm - Dinosaur Take Over Show

7:00pm - Miss Windsor Crowning
Septemberfest Main Stage Rain Location Windsor United Methodist Church

7:30pm - Adult Pageant Crowning
(Contest Judging Aug. 2 At Windsor Senior Center)

Aug 29,2025

5pm - Dinosaur Take Over Show
Free, Former Umb Bank Parking Lot

5:30pm - Baby Show Registration
Septemberfest Main Stage Rain Location Windsor United Methodist Church

6pm - Dinosaur Take Over Show

5-10pm - Carnival

6pm - Baby Show Septemberfest Main Stage

5:30-8:30 - Train Rides Free, First Christian Church

7:00pm - Dinosaur Take Over Show

7:30pm - Man and Woman Of The Year
Septemberfest Main Stage

8pm - Tracy Allison and The Drive
Septemberfest Main Stage

Aug 30,2025

7am - Rock Island Run Registration Katy Trailhead

7:30am - Rock Island Run

10am - 2pm - craft Show Windsor Elementary School

10am - Petting Zoo

10pm - Former Umb Bank Parking Lot

9am - Pet Show Registration
Septemberfest Main Stage

10am - Auto Show Registration

12:30 Pm - Farrington Park

9:30am - Pet Show Septemberfest Main Stage Area

10am - Parade Line Up Windsor High School

11am - Septemberfest Parade
1pm - Cornhole Tournament Registration
Tk Building Supply

1pm - Auto Show Judging Farrington Park

2:30pm - Auto Show Winners Farrington Park

2pm - Cornhole Tournament Tk Building Supply

10am-12pm - Dessert Auction Drop Off T.H. Rogers

5-10pm - Carnival

5:30-8:30 - Train Rides Free, First Christian Church

7pm - Dessert and Pie Auction Septemberfest Main Stage Auction Of Pies, Baked Goods, And Donated Items

8:15pm - Lighted Semi Truck Parade
Line Up 7:30 P.M. At Tk Building Supply Parking Lot

8:30pm - Presley Septemberfest Main Stage

Aug 31,2025

6pm - Truck And Tractor Pull
Pulling In 2025 In Honor Of Bill Hamilton Windsor Rodeo Grounds

Date: August 28-31,2025

Location: Various Venues in Windsor,MO

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