September in Osceola: Food, Fun & Fall Vibes!

As summer fades and the crispness of fall rolls in, Osceola comes alive with a calendar full of can’t-miss events. This September, the town is serving up everything from seasonal bites and festive markets to live music and family-friendly fun. Whether you’re here for the flavors, the festivities, or simply the small-town charm, there’s something happening every week to make your September unforgettable.

Harvest Barn Marketplace & Fun Farm

It’s officially fall, and no season feels complete without a trip to Harvest Barn Marketplace, Southern Iowa’s favorite fall destination for the past 25 years. Tucked inside a restored 1930s barn, this Osceola gem is overflowing with pumpkins, mums, gourds, squash, Indian corn, and all the cozy fall vibes you could ask for.

Beyond the barn doors, families can head out to the Fun Farm, where kids can explore, play, and laugh their way through activities designed to make fall magical. From pumpkin picking to barnyard adventures, it’s a place where imaginations run wild and traditions take root.

Harvest Barn Marketplace has been creating unforgettable memories for a quarter of a century. As they celebrate 25 years, we raise a caramel-drizzled fudge square to the team that continues to bring flavors, fun, and family traditions to life in Osceola.

Bourbon Heritage Month at Revelton Distillery

Celebrate Bourbon Heritage Month all September long at Revelton! From handcrafted spirits and guided tours to Saturday night live music, Revelton has it all. Raise a glass of their rich, flavorful bourbon: neat, on the rocks, or in a cocktail; and toast to craftsmanship, community, and Iowa pride.

Clarke County Farmers Market

Tuesdays & Saturday

Crisp apples, colorful gourds, bright pumpkins, baked goods, handmade crafts, and more, you’ll find all the flavors of fall at the farmers' market. It’s the perfect way to celebrate the season and connect with your community.

Restaurant Week

September 15-21

Get ready to taste your way through Osceola this week with fall-inspired dishes and drinks; while eating local, supporting local, and having fun along the way. Fall for our local restaurants this season and discover flavors you’ll only find right here in Osceola!

Plus, don’t miss your chance to enter the Restaurant Week Giveaway by scanning the QR code at participating restaurants for a shot at a gift card.

Paws in the Park Dog Walk

Saturday, September 20 | 9 AM–12 PM | East Lake Park
Bring your best friend (the furry kind) for a tail-wagging good time at East Lake Park! Registration ($20) includes a dog bandana, treats, and a park map. Enjoy agility demos, photo ops, dog art, and meet local vets, trainers, and groomers.

Ivy Rose Annual Alley Sale

Saturday, September 20 | 4–7 PM

Hunt for hidden treasures, sip and snack as you shop, and score unbelievable deals at this beloved alley-side tradition. This year brings even more fun, The Grassroots Home is joining in, so you’ll have twice the reason to browse, mingle, and shop local!

Chili Cook Off & Street Party

Presented by Hotel Osceola
Sunday, September 21 | 1–7 PM
What’s better than chili, cars, and live music? Add in vendors, raffles, and giveaways, and you’ve got yourself a perfect fall afternoon.

Preacher Lawson Live at Lakeside Hotel Casino

Tuesday, September 24 | 7 PM | Lakeside Hotel Casino

Get ready to laugh until it hurts! Catch comedian Preacher Lawson from America’s Got Talent. Tickets: VIP $47.54, GA $36.13.

Grab your tickets here!

Annual Heritage Day Celebration

Sunday, September 28 | 12–5 PM | Clarke County Museum
Step back in time with games, crafts, tours, and stories of Clarke County’s past. Admission is just one canned food item per person to support the local food pantry.