From the rolling Ozark hills to the banks of the Mississippi River, Missouri celebrates autumn with small-town flair, warm smiles, and plenty of reasons to pull on a sweater. Whether you’re sipping local wine in Hermann or hunting for ghosts in Hannibal, these Missouri festivals capture the heart of fall.
🍺 Oktoberfest in Hermann — Hermann (Oct 24–27, 2025)
Set along the scenic Missouri River, Hermann transforms into a mini-Munich each October. Traditional German music, dancing, local wines, and hearty food fill the cobblestone streets, while vendors sell strudel and souvenirs. Grab a bratwurst, toast with a stein of beer, and enjoy the vineyards bursting with autumn color.
👻 Haunted Hannibal Week — Hannibal (Oct 25–31, 2025)
This historic river town—once home to Mark Twain—takes spooky season seriously. The Haunted Hannibal tours explore ghost stories, candle-lit cemeteries, and mysterious tales from the town’s storied past. Visit the Haunted House on Hill Street, browse costumed street performers, and join in Halloween festivities that are equal parts eerie and fun.
🎃 BooFest — Chillicothe (Oct 31, 2025)
Downtown Chillicothe comes alive with costumed parades, trunk-or-treats, pumpkin-carving contests, and live entertainment. It’s a wholesome, family-friendly event where kids load up on candy and adults enjoy the charm of a community that knows how to celebrate fall without losing its small-town heart.
🍁 Downtown Fall Fair — Perryville (Nov 1, 2025)
For a true slice of Americana, head to Perryville for crafts, handmade goods, food trucks, and live music on the courthouse square. The Downtown Fall Fair marks the shift from pumpkins to Christmas décor, offering early holiday shopping in a charming Main Street setting.
🎄 Sugarplum Festival — St. Joseph (Nov 6–8, 2025)
This beloved tradition officially kicks off the holiday season in St. Joseph. The Sugarplum Festival features artisan booths, gourmet treats, and festive decorations that make downtown sparkle. Expect warm cocoa, local entertainment, and just enough Christmas cheer to bridge fall into winter.
🌾 Rhymers Ridge Harvest Festival — Rhymers Ridge Farm (Oct 27, 2025)
Celebrate the harvest season surrounded by rolling countryside at Rhymers Ridge Farm. Enjoy hayrides, pumpkin picking, apple cider, live bluegrass music, and a sunset bonfire. It’s the perfect quiet stop for glampers looking to soak in the simplicity of rural Missouri life.
🚐 Plan Your Missouri Getaway
Whether you’re ghost-hunting, craft-shopping, or chasing the scent of mulled cider, Missouri’s small-town festivals promise an unforgettable fall road trip. Don’t forget to pair these events with scenic drives through the Ozarks or along the Great River Road.
👉 Continue your autumn tour: Tennessee, Mississippi, Arkansas, Kentucky, and Georgia.