Windsor Septemberfest

Celebrating its first year in its new home, come on out to the Semi Truck Show Saturday afternoon at Windsor High School! Registration begins at 1 p.m. Trucks cannot park for the event until AFTER the conclusion of the parade. Judging will take place at 3:30 p.m. with winners announced at 4 p.m. Trucks can stay in place for the lineup at for the semi truck parade, begins at 7:45 p.m.

Thank you to our sponsor, B&B Truck Repair!

No better location for the SeptemberFest Car Show than Farrington Park! Showcasing cars, trucks, motorcycles and tractors. $15 per entry. Food provided by KnotHedz Mobile and Mallory's Munchies.

Thank you to our sponsors, Apex Mechanical, LLC. and Guardian Insurance.

To see awards categories and pre-register online, visit https://www.windsorseptemberfest.com/forms-flyers/car-show-registration

Do you have a classic car, truck, tractor or semi-truck? We have parade opportunities for you! Line up for both parades is at the Windsor High School Parking lot. All vehicles are invited to participate in their respective vehicle shows after the parade concludes: Cars, Trucks, Tractors and Motorcycles at Farmington park, Semi Trucks at the High School Parking Lot.

Don't miss the SeptemberFest Craft Show! 20+ craft, handmade goods and food vendors will be showcasing their products from 9 a.m. to 2 p.m. at Windsor Elementary School. Before Dawn will be serving breakfast in the school's circle drive, and Windsor Music Boosters will serve walking tacos for lunch.

The Rock Island Run 5k is fun for all ages! Participants in the 5k will run (or walk!) down the Katy Trail to the Rock Island Spur and loop back to the Katy Trailhead. Last year was one of our largest 5ks to date, help us meet, or surpass last year's numbers! Tag your running buddy below and share this post with friends and family!

Register online at https://runsignup.com/Race/MO/Windsor/Septemberfest5kRun

Thank you to our sponsors, Golden Valley Memorial Healthcare, Schreiber, and Hadley Funeral Home.

We are so excited to have inflatable games and bounce houses at SeptemberFest! Here’s all you need to know:

🎯 Games include bounce houses, slides, obstacle courses, jousting and a soccer ball dart game. 3 bounce houses will be ONLY for children 5 and under, those will be located between the Lenora Blackmore Public Library and the former UMB drive through. All other inflatables in the bounce house area are for ages 6+, volunteers will do their best to let like aged children into the games at the same times.

💵 Wristbands are $5 for children 5 and under, $10 for children 6+. Wristbands are good for ONE night of unlimited bouncing fun! Please purchase your wristband nightly at the SeptemberFest ticket booth located at the entrance of the bounce house area. Cash and card accepted. There will be no presale of wristbands prior to the event.

🚫 No shoes, food, or sharp objects will be allowed in the bounce houses.

💕 Please be respectful of others who are playing. Rough housing will not be tolerated, volunteers have the right to confiscate wristbands if rules are not followed.

🙌🏻 Last but not least, a huge THANK YOU to our volunteers who are making this possible! Thursday night volunteers will be from Windsor Assembly , Friday night volunteers will be from Windsor High School students and staff, Saturday night will be staffed entirely by ShipShape Party Rentals, LLC who have been so kind to help us bring inflatable fun to Windsor! Please be kind to our volunteers, and thank them for being there!

There will be free - yes free - face panting at SeptemberFest! Get your face painted Thursday or Saturday night by artist Becky King. Becky will have a donation bucket for St. Jude Children's hospital. She does free face paining, but asks you donate what you can to the children's hospital, a cause that is important to her. Thank you, Becky, for coming to SeptemberFest!

We encourage you to shop local during SeptemberFest! Local businesses, please comment below with any special hours or deals you have going on during SeptemberFest. Many of these businesses are sponsors, and we encourage you to stop by and see them while you're enjoying SeptemberFest activities!

The 2026 SeptemberFest Man and Woman of the year will be announced Friday night at 7:30 p.m. We invite the community to come out and support the recipients of this year's honors.

Thank you to our sponsors, Windsor Area Chamber of Commerce (Windsor, MO) and Heany Law.

It's almost time for Karaoke! Friday night, September 4, from 8 p.m. to 10:00 p.m. at the Cerberus Main Stage. We'd love to see all our local Windsor voices come out and sing! Tag a friend below you know can knock it out of the park. No pre-registration needed - just come ready to sing!