
sebastian-julian / E+ / Getty Images Plus
SEPTEMBER
Plaza Art Fair | September 22–24
Kansas City, 4 hours
Hosted at Kansas City’s Country Club Plaza, the popular art fair spans nine city blocks and tends to draw a crowd of around 250,000. The fair include nearly 250 artists, three music stages, and more than 20 local restaurant booths.
Liberty Fall Festival | September 22–24
Liberty, 3 hours, 45 minutes
More than 200 food vendors and arts and crafts booths will be on hand, selling food, fresh produce, artwork, decor, jewelry, ceramics, metalwork, clothing, quilts, photography, and more. Adults will appreciate the well-stocked beer garden and performances from local and regional artists, while kids can flock to the carnival rides and other family-friendly experiences.
Oktoberfest | September 30
Jefferson City, 2 hours
Highlights include the Muenchberg Beer and Wine Garden, the Mid-Mo Old Car Club show, stage performances, a Kids’ Corner, and a Dachshund Derby. Local craft and food vendors will also be on site. Located in the historic south side of Jeff City, the festival will be primarily located on Broadway, Dunklin, and Washington streets.

Photography by Kevin A. Roberts
Hermann
OCTOBER
Oktoberfest | Weekends, September 29–October 29
Hermann, 1 hour 30 minutes
Each year, Hermann celebrates its German heritage with Oktoberfest. During popular festival, enjoy sweeping views of fall foliage, live music, delicious food, wine, and beer. And on Saturday nights, Jaycees Biergarten (231 E. 5th, Hermann) hosts a stein-hoisting contest. Read more here.
Legends & Lanterns | October 14–15, 21–22, 27–29
St. Charles, 30 minutes
A true testament to the spirit of spooky season, the annual Legends & Lanterns festival takes inspiration from past Halloween traditions and stories. The festival draws from historical rituals of the Druids and Victorians, American ghost stories, traditions of the Day of the Dead celebrated in Mexico, Brothers Grimm fairy tales, and more to create an enjoyable event for all ages.
Apple Butter Festival | October 28–29
Kimmswick, 30 minutes
A large part of the Apple Butter Festival centers around apple butter prepared by the Kimmswick Historical Society. Nearly 100,000 people visit the festival every year to enjoy treats from more than 500 food, drink, and craft vendors. Live entertainment, such as bluegrass, country rock, and dulcimer music, is also part of the small town’s festival. For children, the festival has a petting zoo, pony rides, and a miniature train.

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Homemade Sweet Apple Butter with Cinnamon and Nutmeg
Eureka Scarecrow Festival | Throughout October
Eureka, 30 minutes
More of a prolonged pseudo-scavenger hunt than a festival, the Eureka Scarecrow Festival lasts the entire month. Residents of Eureka celebrate the season by crafting scarecrows to place outside of homes, churches, businesses, and schools. First-, second-, and third-place winners earn cash prizes, awarded by the Eureka Missouri Chamber of Commerce.