Old Webster and Old Orchard: Same Zip Code, Opposite Momentum This Fall

Nine months ago, DD Mau packed up its kitchen on Allen Avenue and moved to Big Bend Boulevard. It wasn't a move out of Webster Groves. It was a move between Webster Groves' two downtowns, and it tells you more about where the city's energy is heading this fall than any single restaurant opening could on its own.

If you live here, you already know the two districts by feel more than by name. Old Webster is the brick-and-storefront strip along Lockwood Avenue between Gore and Elm, the one with the century-old buildings and the porch-light glow after dinner. Old Orchard is the newer commercial pocket on Big Bend Boulevard at South Old Orchard Avenue, the one built around storefronts like Betty's Books and the Frisco Barroom, with a farmers market that rotates through its parking lots each season. Both are walkable. Both host a signature event every year. And right now, they are not telling the same story.

A restaurant voted with its lease

DD Mau opened its original Webster Groves location at 20 Allen Avenue, inside the Old Webster district. This past November, the restaurant relocated to 8169 Big Bend Boulevard, the former home of Weber's Front Row, into a space that seats 150 guests with an expanded menu and a larger kitchen than either its original Maryland Heights location or its former spot on Allen Avenue. That is not a business chasing foot traffic in the abstract. That is a specific owner choosing Old Orchard's larger, newer commercial stock over Old Webster's historic one, and it is the clearest single data point behind everything else happening in the two districts this year.

What's filling in on Big Bend

Old Orchard has spent this year absorbing space rather than losing it. The DD Mau relocation is the most visible piece, but it isn't the only one. A few blocks down Big Bend, a large-scale mural by Webster Groves native muralist Peat "Eyez" Wollaeger is going up on the southwestern wall of the Climate Masters building at 8027 Big Bend, approved by longtime owner Tom Becker. It's the kind of project a business district commissions when it expects people to keep walking past that wall for years, not months.

The district's rhythm backs that up. The Webster Groves Farmers Market has rotated its 2026 season between two sites, one of them Oakwood Salon and Amy's Cake Pop Shop right on Big Bend, drawing a mix of farmers, bakers, food trucks and local artisans within a block of Old Orchard's storefronts. Betty's Books, the Frisco Barroom, the Annex, Papillon Press, David's Guitar and Civil Alchemy all sit within that same short run of storefronts, close enough together that the Old Orchard Fall Festival uses the public lot behind several of them as its staging ground.

Smaller moves on Lockwood

Old Webster's changes have been smaller in scale and slower to arrive. One of the district's more notable recent additions is 23 West Coffee, which opened at 23 W. Lockwood in early 2025, a build-out years in the making from owner Rich Elias on a parcel that once held the Gerber Chapel mortuary. It's a single storefront, not a tripled kitchen or a building-sized mural. The rest of the strip, the Hub Bicycle Co., Euclid Records, the Webster Groves Bookshop, Yucandu Art Studio, Sweetie's Candy & Cones, still lines Lockwood between Gore and Elm much as it has for years, in buildings that date to the 1880s through the 1920s along Gore near the old railroad tracks.

That mix of long-tenured shops and one careful new addition is a different kind of momentum than Old Orchard's. Old Orchard is filling gaps with bigger bets. Old Webster is holding its shape, adding one storefront at a time inside buildings that have stood for more than a century.

The fall calendar, mapped onto the divide

The two districts don't just differ in what's moving in and out. They host their signature fall events on almost opposite ends of the calendar, which makes the choice between them this season fairly concrete.

The Old Webster Jazz & Blues Festival runs on two stages set up on Gore and Allen avenues, with free admission and free parking, and it has grown into an event that draws well over 12,000 people over the course of the day. It's built for the district it's in: a long evening on foot, dinner at one of the sit-down spots on Lockwood, then music until 11 p.m.

The Old Orchard Fall Festival takes over Big Bend Boulevard for a full weekend, with vendors and live music staged in the public lot behind the Frisco Barroom, the Annex, Papillon Press and David's Guitar, and a petting zoo set up behind Civil Alchemy. Last year's edition drew more than three dozen regional artists alongside food trucks, live music and a vendor market that filled the district for two days. It's a daytime, family-oriented event built around browsing rather than a single long sit-down.

Picking your fall based on what you actually want

Given how differently these two events are built, the choice mostly comes down to what kind of evening or afternoon you're after.

• Want a long, music-heavy night out with dinner built in? Old Webster's Jazz & Blues Festival on September 19 is the one to plan around, with free admission and free parking that make it easy to stay for the full stretch from 1 p.m. to 11 p.m.
• Want a full day of browsing, kids' activities and a market feel? Old Orchard's Fall Festival weekend on October 24 and 25 covers more ground over more hours, spread across the district's storefronts and parking lots.
• Curious which district's storefronts will look different a year from now? Old Orchard is the one to watch first. A restaurant moving into a much larger space and a muralist committing wall space to a building are both bets on where the neighborhood is headed next, and neither happens without some confidence that people will keep showing up.

None of this requires choosing sides permanently. Both districts sit inside the same city, a short drive apart along Big Bend and Elm, and plenty of residents treat one as the sit-down dinner spot and the other as the Saturday morning errand run. What's worth paying attention to this fall is that the two are no longer just parallel versions of the same small-town Main Street. One is filling in with bigger footprints. One is holding its shape one storefront at a time. Which approach ages better is the kind of thing you only find out by watching both over the next year.

If you're watching Webster Groves for reasons beyond a Saturday night out, whether that's a future move, a home you're weighing whether to sell, or just curiosity about what a shifting business district can mean for property values nearby, Susan Hurley Homes has spent years tracking these neighborhood-level details across the St. Louis metro. Request a complimentary consultation whenever you're ready to talk specifics.