You already know the drill if you've lived near Big Bend Boulevard for more than one October: park early, expect crowds, bring cash for the food trucks. What you might not know yet is that this year's Old Orchard Fall Festival isn't the same event you're picturing. It grew, in ways you can actually measure, and at least one thing that showed up last year won't be there this time.
The festival runs Saturday, October 24, and Sunday, October 25, 2026, both days from 10 a.m. to 6 p.m., stretching along Big Bend Boulevard between Dale Avenue and Summit Avenue. If that sounds familiar, the footprint is the part that hasn't changed. The event has changed in a few other ways.
A Second Street, Not Just More Of The Same
For the first time, organizers are closing Log Cabin Lane, the stretch running between Big Bend Boulevard and East Frisco Avenue, and turning it into a second festival hub. In past years, the festival's vendors and music stayed clustered around the public lot behind The Frisco Barroom, The Annex, Papillon Press, and David's Guitar, with the petting zoo tucked behind Civil Alchemy. This year the Merchant & Business Association of Old Orchard is spreading the event onto an entire additional street rather than packing more into the same lots.
That matters if you're the kind of local who plans your route through the festival by memory. The old mental map, one main strip with everything crammed behind a few storefronts, doesn't cover the whole event anymore. Give yourself extra time to wander Log Cabin Lane along with Big Bend, especially if last year you cut through in twenty minutes and called it done.
Two Stages, For The First Time
Last year's lineup ran on what amounted to one stage: Neil Salsich, Falling Fences, Voodoo Acoustic Dead doing their Grateful Dead tribute set, the Webster Community School Jazz Band, and Colonel Ford among the names on the bill. This year, the festival is running two live stages for the first time, with 14 bands confirmed across the weekend. The names announced so far include Jake's Leg, Voodoo Funky Butt Brass Band, The Brothers Lazaroff, and the Webster Groves High School Jazz Band, with organizers saying more acts are still to be added.
Two stages running simultaneously changes how you'll want to plan a Saturday afternoon here. You won't be able to catch every act by standing in one spot the way you might have in past years. If a particular band matters to you, check the schedule before you go rather than assuming you'll wander into it.
More Than 50 Vendors, Up From Roughly 36
The vendor marketplace saw a similar jump. Last year's festival hosted more than 36 regional artists and makers. This year's official count is 55 plus vendors and regional artisans, better than a 50 percent increase. Confirmed names so far include Crispy Sips, Glow Candle Co., Steele Caramels, and Everyone's Republic, alongside Old Orchard's permanent shops, which stay open and running their own specials throughout the weekend.
If you've been to this festival before and remember it as a manageable afternoon of browsing a couple dozen tables, budget more time this year. A vendor list that's grown by nearly twenty names doesn't fit into the same hour you used to set aside.
What Didn't Make This Year's Announcement
Here's the part worth knowing before you plan your evening around it. Last year's festival explicitly paired with a Webster Groves Farmers Market at Night, held at Oakwood and Big Bend from 4 to 9 p.m. Saturday, with food and drink vendors including Fil-Am Fusion, Off Elm, Do More Good Coffee, and Crispy Sips. This year's official festival announcement doesn't mention a farmers market component at all.
That's consistent with a broader shift for Webster Groves' farmers market scene this year, which has moved between locations and sponsors more than once recently. If a Saturday night market next to the festival was part of your plan, don't count on it showing up this time. Check directly with the Old Orchard Business District closer to the date if that's the piece you're building your evening around.
One more scheduling note for anyone going off memory from last year. In 2025, Saturday hours ran until 9 p.m. This year, both Saturday and Sunday wrap at 6 p.m. If you were planning to swing by after dinner the way you could last October, you'll want to move that up.
The Practical Stuff
A few details worth having before you head out:
- Trick-or-treating at participating Old Orchard businesses runs Saturday, October 24, from 3 to 5 p.m.
- The "Find the Ghost" Bingo Contest sends you around the district hunting clues, with completed cards due by 3 p.m. Saturday for a shot at a prize drawing.
- Cowboy Critters Petting Zoo returns for another year, with goats, pigs, donkeys, horses, ducks, and rabbits on hand for anyone bringing kids.
- This year's presenting sponsors include Labatt Blue, 4Hands, the City of Webster Groves, and STL Bucket List.
None of this requires an RSVP. It's free and open, same as it's been in past years. The difference this time is scale, not admission.
If You Want Dinner After
A short drive puts you in Old Webster, the historic business core along Lockwood Avenue, which is a separate stretch from the Old Orchard district hosting the festival. Two blocks there are anchored by O+O Hospitality, the restaurant group behind Olive + Oak, O+O Pizza, and Clover and the Bee, which runs as a daytime café and turns into a natural wine bar on Thursday through Saturday nights. A short walk down the same street puts you at Madrina, the Italian American restaurant that took over the historic Gorlock Building after C.J. Muggs closed there, serving dishes built around whole roasted chickens and hand-cut pastas.
If the festival crowd wears you out by late afternoon, this is where most of your neighbors end up anyway. Neither district competes with the other. They're two separate walkable pockets of the same small city, and this particular weekend gives you a reason to hit both.
Fall in Webster Groves has a way of turning into a full Saturday without you planning it that way. A festival that used to take an hour now covers two streets, two stages, and more vendor tables than it did twelve months ago. Whether you're catching the Webster Groves High School Jazz Band on one stage or working your way down the new stretch of Log Cabin Lane, it's worth knowing you're looking at a bigger version of the event than the one you remember.
Webster Groves keeps changing in small, countable ways like this, whether it's a festival adding a second street or a business district shifting which markets show up on a given weekend. If you're the kind of person who likes knowing what's actually different from one year to the next, whether that's a festival footprint or a neighborhood's housing stock, Maureen Onder has spent more than three decades paying attention to exactly that kind of detail across Webster Groves and the surrounding suburbs. Call for a local market consult whenever you're ready to talk about what's next for your own address.
