Old Orchard's Fall Festival Returns This October

WEBSTER GROVES, Mo., Sept. 1, 2026 /PRNewswire/ -- Autumn is coming back to Big Bend Boulevard. The Merchant & Business Association of Old Orchard (MBAOO) invites the community to this year's Fall Festival, taking place Saturday, October 24 from 10:00AM to 6:00PM and Sunday, October 25 from 10:00AM to 6:00PM. This two-day event will transform Big Bend Boulevard, from Dale Avenue to Summit Avenue, into a seasonal celebration. New this year, Log Cabin Lane, between Big Bend Boulevard and East Frisco Avenue, will close to traffic and open up as a festival hub packed with music, shopping, and fall activities for all ages.

This Year's Sponsors: Labatt Blue, 4Hands, City of Webster Groves, and STL Bucket List.

What's Happening This Year

Two Stages, Nonstop Music
 For the first time, the festival is expanding to two live music stages, giving guests twice the entertainment across the weekend. Fourteen bands will perform over the two days, including Jake's Leg, Voodoo Funky Butt Brass Band, The Brothers Lazaroff, and the Webster Groves High School Jazz Band, with more acts to be announced.

A Bigger Marketplace
This year's festival brings together 55+ vendors and regional artisans, offering everything from handmade goods to unique fall finds. Confirmed vendors include Crispy Sips, Glow Candle Co., Steele Caramels, and Everyone's Republic.

Cowboy Critters Petting Zoo
A festival favorite is back — the Cowboy Critters petting zoo returns for another year, giving kids and adults the chance to meet goats, pigs, donkeys, horses, ducks, and rabbits up close.

"Find the Ghost" Bingo Contest
Keep an eye out around Old Orchard for the "Find the Ghost" Bingo Contest. Completed bingo cards can be turned in by 3:00PM on Saturday, October 24 for a chance to win a gift basket.

Food on Every Corner
Hungry festival-goers can choose from Old Orchard's own restaurants or grab a bite from food trucks parked throughout the marketplace, including Lomito Bonito and FarmTruck.

District-Wide Events: More to Explore in Old Orchard
The festival marketplace is just part of the fun — Old Orchard's shops and restaurants will be running specials, activities, and live music of their own throughout the weekend. Follow @oldorchardwg on Instagram or Old Orchard–Webster Groves on Facebook for the latest updates, and visit our website at https://www.oldorchardwebstergroves.com/ for more.

Trick-or-Treat
Old Orchard businesses will welcome trick-or-treaters on Saturday, October 24, from 3:00PM to 5:00PM.

About Old Orchard
Nestled in Webster Groves, the Old Orchard Business District is a hub of independent shops, restaurants, cafés, and community spirit. Throughout the year, Old Orchard brings neighbors together through events centered on food, music, art, and connection.

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SOURCE City of Webster Groves