Windsor Septemberfest

09/01/2026

Sorry for any disappointment. Blame the weather and the fact that these little guys are cold-blooded.

09/01/2026

We hope you are making plans to attend SeptemberFest! We're excited for all the fun and actives that will be going on this weekend as we celebrate small town life in a big way for the 21st year!

**Update, due to the forecasted heat, the reptile exhibit is canceled. The petting zoo and pony rides will continue as planned.

Check out our updated schedule of events! Windsor 4Co Rural Fire will be doing a duck derby Thursday and Friday evening on Benton Street in front of the IOOF building. All proceeds from the duck sales will help fund the 2027 4th of July firework show at Farrington Park. The location of the petting zoo and pony rides has been changed from the former UMB Bank parking lot to Benton street in front of the Windsor Historical Society. The UMB Bank parking lot will be used for bounce house volunteer and vendor parking only.

09/01/2026

Did you know....

SeptemberFest is a member of Missouri Association of Fairs and Festivals. This makes the young lady crowned Miss Windsor eligible for the 2027 pageant at the Missouri State Fair, assuming she meets their additional requirements. This year, for the first time, all three Miss Windsor candidates are of the age that they meet the Missouri State Fair age requirements and can go on to compete at the Missouri State Fair in 2027. This is in addition to the $250 scholarship Miss Windsor receives from SeptemberFest.

Further, the Pedal Pull winner is also eligible to compete at the Missouri State Fair Pedal Pull in 2027.

Please come out and support both the pageant and pedal pull participants Thursday and Friday night as they compete for an opportunity to be at the Missouri State Fair in 2027!

09/01/2026

The Windsor Historical Society will be selling raffle tickets for 6 items and baskets they will be raffling off Saturday night. The drawing will take place at the intermission of the Wildwood Boys, around 9:30 p.m. at the Cerberus Main Stage. Stop by the Historical Society's booth at the corner by Heany Law Friday and Saturday to purchase your tickets! Proceeds help support the work of the Historical Society and Museum.

08/31/2026

SeptemberFest is excited to welcome Wildwood Boys to town Saturday night!

Wildwood Boy's Journey started in the year of 2010 with five guys who wanted to play bluegrass music. It was then we heard the likes of Bill Monroe, Flatt and Scruggs and other tradional bands. That soon progressed to cross over counrty music, gospel, original music in a bluegrass style including three studio recordings multiple live shows throughout Missouri and Kansas. As they enter their 16th year they are excited to introduce themselves to Windsor!

David Batson - Banjo and Vocals
Chris Spriggs - Bass and Vocasls
Gary Winders - Mandolin and Vocals
Jeremy Magers - Fiddle
David Bullock - Guitar and Vocals

08/31/2026

Does this really need advertising??? The Lighted Semi Truck parade is back again! New line up location at Windsor High School, beginning at 7:30 p.m. The lineup will follow the morning parade route to Main Street via North, Mill and Florence Streets before rolling down Main Street.

08/31/2026

New to SeptemberFest is the Pedal Pull! For ages 4-12. Register starting a 5 p.m. at the Cerberus Main Stage area. Pull begins at 5:30 p.m.

Thank you to Windsor, Missouri FFA Chapter for putting this event on and to B&B Truck Repair for sponsoring it!

08/31/2026

This year's corn hole tournament is not one to miss out on! Competitive pool is $1000 to win. Register on Saturday from 1-2 p.m. at TK Building Supply. Tournament begins at 2 p.m.

08/31/2026

Last year we had 129 signed up for the Rock Island Run.... do you think we can surpass that?? Register today to help us make this SeptemberFest's largest 5k to date!

08/31/2026

121 Farmhouse Kitchen will be one of our Saturday vendors! Check them out from 9 a.m. to 2 p.m. in front of Golden Valley Medical, Windsor on Benton Street!

🍂 **Starting September off with a BANG!** 🍂

It’s finally the **“-BER” months** and I am READY! 🙌 Now if Mother Nature would just get the memo and turn that temperature down a little… 😂🍁

And BIG NEWS — **the Mobile Market is BACK this week!** 🚚🛍️ We’ve got a busy week ahead with plenty of chances to shop 121!

❤️ **Thursday:** Find the Mobile Market at **UCM Get the Red Out** from 4–6:30pm!
🍂 **Saturday:** We’re headed to **Windsor Septemberfest** from 9am–2pm!

PLUS the Market will be open throughout the week, so check out the schedule below and plan your 121 stop! 👇

Fresh produce 🥕 • baked goods 🍪 • local favorites 🥛 • gifts 🛍️ • fall goodies 🎃 and SO much more!

**Hello September — we’ve been waiting for you!** ❤️🍁🏈

Who else is ready for **cool mornings, football, pumpkins, mums and ALL THINGS FALL?!** 🙋‍♀️