Every third Saturday in September, Gore and Allen avenues turn into two stages, a few thousand lawn chairs, and eleven hours of jazz, blues, and gospel that nobody in Webster Groves has to pay a dime for. This year's date is Saturday, September 19, running 1 p.m. to 11 p.m. The Webster-Kirkwood Times counted last September's edition as the festival's 23rd year, which makes this one the 24th. If you've lived here more than a summer, you already know the drill: park at the public garage or the South Gore lot, bring a chair, expect the Webster Groves High School Jazz Band to open and a gospel set to land somewhere in the middle of the day.
What you might not know is that one of the two streets hosting this year's festival used to be home to a restaurant that packed up and left for a bigger space a few blocks north. That move, and a few others like it, say something about where Webster Groves is actually putting its money right now. It isn't on Allen Avenue.
Twenty-Four Septembers On Gore And Allen
Old Webster's commercial identity goes back further than the festival, further than most of the businesses currently in it. The district traces to the early 1850s, when Augustus Moody built a post office and general store next to the Pacific Railroad tracks, roughly forty years before Webster Groves incorporated as a city at all. The jazz festival is a modern addition to that history, but it fits the same footprint: the festival happens on two streets in the historic Old Webster business district, with free parking suggested at the public garage, the South Gore lot, or the lot west of Straub's on Lockwood.
Last year's lineup ran eleven bands across the two stages, with the Webster Groves High School Jazz Band kicking things off early and community favorites like Marquise Knox closing out one of the stages later in the night. Food and drink come from the restaurants already lining Lockwood and Gore, so the festival doubles as a sampler plate of whatever the district is currently serving. That detail matters more than it sounds like it should, because what the district is currently serving has been shifting.
The Restaurant That Used To Be Right Where The Music Plays
DD Mau, the Vietnamese spot that built a following on Allen Avenue, outgrew that space and relocated to 8169 Big Bend Blvd. in Old Orchard on November 21, 2025. Allen Avenue is one of the two streets the jazz festival closes off every September. So the same block that hosts one of the festival's stages lost a restaurant to the district a few minutes' walk to the north.
That's not an isolated data point. Track the two districts across this year and they read as moving in opposite directions: Old Orchard has spent the last several months absorbing new tenants, while Old Webster is in the middle of a tenant reshuffle that will change what a Friday night walk down Lockwood looks like by winter. If you live on one of the streets that feeds into Lockwood, that split is the more useful thing to track than any single new sign in a window, because it tells you which direction the foot traffic and the investment are actually headed.
Old Orchard's newest visual marker is going up right now. Webster Groves native street artist Peat "Eyez" Wollaeger is currently painting a mural on the southwest wall of the Climate Masters building at 8027 Big Bend Blvd., a project approved by Climate Masters founder and owner Tom Becker. It's the kind of investment a district makes when it expects people to keep showing up, and it's happening a block and a half from where DD Mau just planted its bigger flag.
Here's how the two districts stack up heading into this festival weekend:
| Old Webster | Old Orchard | |
|---|---|---|
| Core blocks | Lockwood Avenue between Gore and Elm, plus Gore and Allen for festival weekend | Big Bend Boulevard at South Old Orchard |
| 2026 headline move | Tenant reshuffle underway on Lockwood, including the space DD Mau left on Allen | DD Mau's larger relocated space, open since November 2025 |
| Longtime anchor | Robust Bistro & Wine Bar, on Lockwood since 2007 | Balkan Treat Box, a storefront since 2019 |
| What's new to see | Reshuffled storefronts worth checking on through the fall | A mural by Peat "Eyez" Wollaeger going up on the Climate Masters building |
Neither district is disappearing. But if you're trying to read where Webster Groves is spending its retail energy this year, Old Orchard is where the newer square footage and the newer public art are landing.
What The Festival's Food Table Doesn't Advertise
The food and drink at the jazz festival come from restaurants already in the neighborhood, and a good number of those kitchens now carry a certification most festivalgoers walk past without noticing. In spring 2025, Webster Groves became the fifth official Green Dining District in the St. Louis region, a designation the Green Dining Alliance awards when at least a quarter of a district's locally owned restaurants meet its sustainability standards. Webster Groves currently has ten GDA-certified restaurants.
Madrina, the Italian-American restaurant that took over the old C.J. Mugg's space at 101 W. Lockwood, earned a 5-star GDA certification for its water and energy conservation and its food sourcing. The restaurant partners with local farms for beef, poultry, eggs, and dairy, makes its pasta by hand, and repurposes vegetable trimmings into staff soups rather than the trash. Robust Bistro & Wine Bar, on Lockwood since 2007, was doing a version of this before the certification existed, specializing in what it calls clean wine sourced from smaller vineyards that farm biodynamically or organically. Over in Old Orchard, Balkan Treat Box, which started as a food truck in 2017 before opening its storefront in 2019, bakes its own bread in a wood-fired oven, sources Missouri beef and local produce, and runs its kitchen entirely on electric power.
None of that shows up on the festival flyer. But when you're eating something from one of Old Webster's restaurant tables on September 19, there's a reasonable chance it came out of a kitchen that has already done the work to earn a certification most of the crowd around you has never heard of.
How To Actually Spend The Day
If you're going, the practical version is simple. The festival runs 1 p.m. to 11 p.m. on Saturday, September 19, on Gore and Allen avenues, with free admission and free parking at the public garage, the South Gore lot, or the lot west of Straub's on Lockwood. Bring a lawn chair or a blanket, since the music happens on the street itself. Expect the day to start with the high school jazz band and move through blues and gospel sets before the evening acts close things out.
The part worth adding to your plan is the walk north. Old Orchard is close enough to Old Webster that treating festival weekend as a two-district outing costs you almost nothing in time. Stop by the new DD Mau space on Big Bend, see how far the Wollaeger mural has come by the third Saturday of September, and compare it against whatever Lockwood's tenant reshuffle has produced by then. The festival will look the same as it did in 2025 and probably the same as it will in 2027. The two blocks around it won't.
If you're the kind of resident who tracks these shifts because you're curious about where the neighborhood is headed, not because you're shopping for a house, that instinct is worth trusting. Webster Groves changes in small, specific ways, one relocated restaurant and one new mural at a time, and the people who notice those changes early are usually the ones who understand the neighborhood best when it actually comes time to make a move. If that day comes for you or someone you know, Welcome Home with Holly is always glad to talk through what a particular block or district is really doing, festival season or not.
