Fall is a beautiful time to explore Historic Missouri Wine Country, where rolling vineyards, historic communities, and local wineries set the scene for seasonal events. Just a short drive from St. Charles, Augusta and Defiance are celebrating the season with harvest festivals, wine tastings, live music, Oktoberfest events, and Halloween-inspired activities. Discover some of the best fall events in Historic Missouri Wine Country to add to your autumn itinerary.
Swingin’ in the Vines
Enjoy a romantic fall evening in Historic Missouri Wine Country at Swingin’ in the Vines on September 18. A ticket includes a pumpkin wagon shuttle ride, picnic basket with food for two, a bottle of wine, a port tasting in an underground wine cellar, and live music by Sweetie and the Toothaches. Don’t forget your camping chairs!

Augusta Harvest Festival
Kick off the harvest season at the Augusta Harvest Festival on September 19 from 9 AM to 4 PM. Find pony rides, a petting zoo, slides, craft vendors, a pie contest, and live music by the Texas Giants in the Augusta Town Square. The celebration also includes the Harvest Parade, which begins at the Harmonie Verein and winds its way to the town square. This year’s parade theme is America’s 250th birthday. After the festival, continue the celebration by visiting nearby wineries as the harvest season begins.

Defiance Oktoberfest
Celebrate Oktoberfest all October long in Defiance! This month-long celebration in Historic Missouri Wine Country features open mic nights, happy hours, brunch buffets, live music, karaoke, and more at local businesses throughout the community. Visit the Defiance Oktoberfest schedule online to see the full lineup of events.

Spirits of the Past at the Historic Daniel Boone Home
Spend a fall evening in Defiance at Spirits of the Past at the Historic Daniel Boone Home on October 10 from 6 PM to 10 PM. Explore the historic village by lantern light as storytellers share tales of generations past at vignettes throughout the grounds. The crisp autumn air and flickering lanterns create an eerie atmosphere as night falls over Historic Missouri Wine Country. Purchase tickets online.

Wicked Wine Hop in Augusta
Gather your friends for a spooky day of wine tasting at the Wicked Wine Hop in Augusta on October 24 from 11:30 AM to 7 PM. Four Augusta wineries will participate, each offering costume contests, live music, and food and drink specials. For an extra dose of Halloween fun, stop by Mount Pleasant Estates for a special spooky cellar tour. Grab your group and spend the day exploring Historic Missouri Wine Country. Tickets are available online and at the door.
Augusta Bottoms Festival
Sample local beer, wine, and spirits while enjoying live music at the Augusta Bottoms Festival on November 7 from noon to 5 PM. This community event features local beverages, live music, shopping with vendors, cigars, and more. Gather with friends and enjoy autumn in Historic Missouri Wine Country. Purchase tickets online.

Make the most of the season with a visit to Historic Missouri Wine Country. Whether you’re sipping wine in Augusta, enjoying live music in Defiance, or celebrating the harvest with friends, there are plenty of ways to experience fall just west of St. Charles.