All the Fall Fun—Freshly Sliced: Fall in Chillicothe, Missouri

Written By Karter — September 15, 2026

There is just something about fall in Chillicothe, Missouri.

The air gets crisp, the trees show off, downtown feels extra cozy, and the calendar fills with festivals, pumpkin patches, live music, local food and reasons to loaf around a little longer.

Whether you are planning a day trip, family weekend, scenic drive or fall getaway in north Missouri, here are some of the best things to do in Chillicothe this fall.

September 12–13: Chautauqua in the Park

One of Chillicothe’s favorite fall traditions returns to beautiful Simpson Park.

Chautauqua in the Park brings together arts, crafts, food, entertainment, demonstrations and family fun under the trees. Wander, snack, shop and explore—then make a weekend of it with downtown dining, shopping, murals and a visit to the Chillicothe Welcome Center and Home of Sliced Bread Historic Building.

September 18–19: CHS Homecoming Weekend

There is nothing quite like Homecoming in a small town. Alumni return, families gather and Chillicothe is filled with hometown pride.

Whether you are coming home or visiting for the first time, it is a great weekend to experience the community spirit that makes Chillicothe special.

September 19: Blues, Brews and BBQ

Art, music and local flavor come together for the Blues, Brews and BBQ Anniversary Celebration at Cultural Corner Art Guild & Gallery.

Add live music, good food and a creative local space to your fall weekend itinerary.

September 25–27: A Full Weekend of Fall Fun

If you are looking for a weekend packed with fall events in Missouri, this one delivers.

Old Time Harvest Days at the Livingston County Fairgrounds celebrates agriculture, history and harvest traditions September 25–26. On Friday, September 25, the Chillicothe Theatre Company presents Starlight: A Musical Revue. On Saturday, September 26, Blackwater welcomes Kricket Alley for an evening of live music.

Keep the fun going Sunday, September 27, at the St. Columban Fall Festival, an annual favorite featuring food, fellowship and hometown tradition.

Harvest fun, theater, live music, local food, shopping and murals all in one weekend? Sounds like a pretty good excuse to stay the night.

Pumpkin Patch Season in Chillicothe

No Missouri fall getaway is complete without pumpkins.

Throughout September and October, visit Papa Charlie’s Pumpkin Patch and Our Mini Farm Pumpkin Patch for family-friendly fall fun, outdoor adventures and seasonal photo opportunities.

Pick a pumpkin, grab lunch, explore downtown and enjoy the fall color. Chillicothe is good at turning a pumpkin-patch stop into a full day of fun.

October 2: Downtown Oktoberfest

Gather your friends for Downtown Oktoberfest in Chillicothe, formerly the Fall Wine Walk.

Enjoy seasonal sips, local businesses, food, shopping and a festive evening in the heart of downtown. It is an easy way to mix a little grown-up fall fun with Chillicothe’s small-town charm.

October 19: Poosey Conservation Area Fall Driving Tour

Looking for fall foliage and scenic drives in north Missouri? Put the Poosey Conservation Area Fall Driving Tour on your list.

This annual favorite offers changing leaves, peaceful countryside and vehicle access to roads not normally open to the public.

Make Chillicothe your home base, enjoy the drive—and maybe take the long way home.

October 30: Boofest in Downtown Chillicothe

Fall ends on a sweet—and slightly spooky—note with Boofest in Downtown Chillicothe, October 30 from 4–6 p.m.

Families can enjoy downtown trick-or-treating and one of Chillicothe’s favorite Halloween traditions. It is cute, cozy and just the right amount of spooky.

Find Your Perfect Slice of Fall

Come for Chautauqua. Come for pumpkin patches, live music, theater, fall festivals, downtown events or brilliant autumn color. Better yet, pick a weekend and enjoy a little bit of everything.

While you are here, stop by the Chillicothe Welcome Center and Home of Sliced Bread Historic Building to discover why Chillicothe is known as the Home of Sliced Bread, grab some trip ideas and start exploring.

This fall, come loaf around in Chillicothe, Missouri.

We think you will agree—it is the greatest thing since sliced bread.