Webster Groves, Mo. – September 07, 2026 -- Autumn returns to Big Bend Boulevard as the Merchant & Business Association of Old Orchard hosts its Fall Festival on Saturday, October 24 and Sunday, October 25, running 10:00AM to 6:00PM both days. The two-day event transforms Big Bend Boulevard between Dale Avenue and Summit Avenue into a seasonal celebration, with Log Cabin Lane closing to traffic for the first time to serve as a festival hub between Big Bend Boulevard and East Frisco Avenue.

Fourteen bands split across two stages this year

For the first time, the festival expands to two live music stages, doubling the entertainment across the weekend. Fourteen bands are confirmed, including Jake's Leg, Voodoo Funky Butt Brass Band, The Brothers Lazaroff, and the Webster Groves High School Jazz Band, with additional acts still to be announced.

More than 55 vendors fill an expanded marketplace

This year's marketplace brings together over 55 vendors and regional artisans selling handmade goods and fall finds. Confirmed vendors include Crispy Sips, Glow Candle Co., Steele Caramels, and Everyone's Republic.

Cowboy Critters petting zoo and a ghost-hunting bingo contest return

The Cowboy Critters petting zoo is back, letting visitors meet goats, pigs, donkeys, horses, ducks, and rabbits. A "Find the Ghost" Bingo Contest also returns, with completed cards accepted until 3:00PM on Saturday, October 24 for a chance to win a gift basket.

Food trucks and district restaurants cover every corner

Festival-goers can eat at Old Orchard's own restaurants or visit food trucks stationed throughout the marketplace, including Lomito Bonito and FarmTruck. Old Orchard shops and restaurants will also run their own specials, activities, and live music throughout the weekend.

Trick-or-treating runs Saturday afternoon

Old Orchard businesses will welcome trick-or-treaters on Saturday, October 24, from 3:00PM to 5:00PM. The festival is sponsored by Labatt Blue, 4Hands, the City of Webster Groves, and STL Bucket List.