Ask a longtime resident where "downtown Webster Groves" is, and the answer splits depending on who's talking. Some point you to Gore Avenue, where the shops and restaurants cluster around the old business district known as Old Webster. Others mean Big Bend Boulevard, a mile or so away, where Old Orchard runs its own storefronts, its own gazebo, its own crowd on a Friday night. Both are right. Webster Groves has never had one town center. It has two, and this September they're each running full calendars that barely overlap.
That's not a complaint. It's the actual mechanism behind what looks, from the outside, like a single town's event schedule. Once you see the split, you start reading the calendar differently, and you notice that even the restaurants have been quietly sorting themselves onto one side or the other.
The Gazebo Series Is Closing Its 21st Season
Old Orchard's contribution to September is the Gazebo Music Series, now in its 21st year at the gazebo on Big Bend Boulevard. It runs six straight Fridays, all free, all starting at 7 p.m., and this year's run started August 21 with singer-songwriter Javier Mendoza, whose songwriting credits stretch back to work for Enrique Iglesias and Ricky Martin before he built his own bilingual roots-rock project. The Red and Black Brass Band followed on August 28 with a jazz-soul-pop set, and The Bishops, an acoustic duo built around brothers Daniel and Matthew Bishop, played September 4.
The next three Fridays are the ones still ahead as of this writing. Jake's Leg, the country's longest-running Grateful Dead tribute band, plays September 11. Neil Salsich, who built a national profile as a contestant on "The Voice," closes out September 18. Diesel Island, a classic and outlaw country cover act, plays the finale on September 25.
None of that requires a ticket. It requires knowing the gazebo is on Big Bend, not Gore.
The Same Saturday, a Different Street Entirely
One night after Salsich's set, Old Webster throws its own event, and it's a bigger one. The Old Webster Jazz & Blues Festival lands on Saturday, September 19, running from early afternoon into the evening on two stages set up on Gore and Allen avenues. It's free, parking is free, and in a typical year it pulls well over 12,000 people into a business district small enough to cover entirely on foot. The festival has been running since 2001, which makes it one of the longest continuously operating jazz festivals in the region, and its footprint has nothing to do with the gazebo scene a mile west.
What's telling is that the city's own event announcement for the Gazebo Series doesn't pretend these are unrelated. The September 18 Salsich show is explicitly billed as happening on the eve of the Jazz Fest, a small piece of scheduling language that tells you the two districts know exactly what the other is doing and are choosing to stand next to it rather than compete with it. They're coordinated. They're still not the same event, on the same street, or for the same audience.
Two Blocks of Lockwood Just Changed Kitchens
Old Webster's restaurant identity runs almost entirely through a two-block stretch of Lockwood Avenue, and it just went through a leadership shuffle. Clover and the Bee, the daytime café that turns into Clover Wine Bar on Thursday through Saturday nights, is part of O+O Hospitality, the same group behind Olive + Oak, O+O Pizza, and Perennial on Lockwood, all sitting within that same short walk. Executive chef Mike Risk recently departed for a move to Spain, and the group is filling the gap by promoting Bonnie Moore to culinary director while Ashley Shelton steps in as executive chef across O+O Pizza and Clover and the Bee. For a restaurant row this compact, a chef change at one address ripples across the whole block, since the same handful of people have been cross-staffing these kitchens for years.
A few doors down, Madrina occupies the space that spent two decades as C.J. Mugg's, the corner tavern that anchored Old Webster before it closed. The new owners gutted the building down to the studs and rebuilt it with a mid-century Italian-American concept, which tells you something about how Lockwood Avenue treats its landmark spaces. Nothing sits empty long, and nothing that reopens looks like what came before it.
The Restaurant That Switched Sides
Here's the detail that makes the two-district split concrete instead of abstract. DD Mau, the fast-casual Vietnamese spot known for its grab-and-go Vietnamese dishes, used to have its Webster Groves location at 20 Allen Avenue, right in the heart of Old Webster near the same Gore and Allen intersection where the Jazz Fest sets up its stages. Late last year, the owners moved that location out entirely and opened a bigger version in Old Orchard, taking over the former Weber's Front Row space at 8169 Big Bend Boulevard. The new location seats 150 and runs a larger kitchen than either the original Maryland Heights restaurant or the old Allen Avenue spot it replaced.
That's not a business closing. It's a business relocating from one half of town to the other, and choosing Old Orchard's foot traffic over Old Webster's. If you've noticed the restaurant scene on Big Bend feeling a little more crowded and the one on Allen feeling a little quieter, that's the reason, and it happened in a single move.
What a September Weekend Actually Looks Like
Put the two calendars next to each other and a resident's month starts to organize itself around a simple rule: check which street the plan is on before making the other plans around it.
| Date | Old Orchard (Big Bend) | Old Webster (Gore/Lockwood) |
|---|---|---|
| Sept 11 | Jake's Leg, Gazebo Series, 7 p.m., free | Regular restaurant row, no event |
| Sept 18 | Neil Salsich, Gazebo Series, 7 p.m., billed as eve-of-festival | Restaurants filling up ahead of the fest |
| Sept 19 | No competing event | Jazz & Blues Festival, Gore & Allen, free, two stages |
| Sept 25 | Diesel Island, Gazebo Series finale, 7 p.m. | Regular restaurant row, no event |
A resident who wants a low-key Friday with free live music and no crowd management heads to the gazebo. Someone planning around the festival needs to think about parking a little earlier and expect Lockwood's restaurants to book up, especially with Madrina and Clover and the Bee both a short walk from the stages. Neither plan requires driving more than two miles, but they're not the same errand.
Why This Matters Beyond September
The pattern isn't unique to September. Each district builds its own programming on its own timeline, and the businesses that serve both, like O+O Hospitality's restaurant group, staff and plan around two audiences instead of one. When a restaurant like DD Mau decides it's outgrown its space, the choice of where to relocate isn't random. It's a bet on which district's foot traffic fits the concept better.
For anyone who's lived here a while, none of this is a surprise. It's just rarely said out loud, because most coverage of Webster Groves treats it as a single, tidy suburb with one main street. It has two, and each one is currently in the middle of its own September.
If you're curious how these two districts show up in the broader character of the neighborhood, from home styles to daily routines, the Webster Groves neighborhood guide and our earlier look at everyday living in Webster Groves go deeper into both sides of town.
Whenever the conversation turns from Friday night plans to real estate, whether that's this year or a few years out, Becky O'Neill has spent decades tracking exactly this kind of block-by-block detail across Webster Groves and the rest of Greater St. Louis. Get Your Home Value whenever you're ready to see what that local knowledge means for your own address.
