Ask someone who lives near downtown Kirkwood what's happening this fall and they'll say Greentree. Ask someone three miles up Big Bend in Old Orchard and they'll say the Fall Festival. Both are right, and both are only telling you about their own half of the neighborhood.
Webster-Kirkwood gets treated as one hyphenated place with one calendar, largely because the real estate listings and the school district maps draw it that way. But the two downtowns run their own civic traditions on their own schedules, funded by their own business districts, and they only really overlap for about a week in late October. If you've lived here a while, you already know your side. What's easy to miss is how the other side's calendar works, and the one stretch of days when both towns are actually doing the same thing at the same time.
Kirkwood's calendar turns fifty, then turns into a pumpkin patch
The Kirkwood Farmers' Market opened for its new season on April 4, and this year that opening carried extra weight. The market was founded by the city of Kirkwood in 1976 as a bicentennial project, which makes 2026 its 50th season. It runs at 150 East Argonne Drive, right between Highway 40 and I-44, and it's owned by the city and run through a Farmers' Market Committee working alongside the Downtown Kirkwood Special Business District. That's a different setup than Webster Groves uses, and it matters for who shows up and when.
Once the market's main season winds down at the end of September, The Summit All Seasons Market takes over the same footprint and turns it into a fall attraction. In recent years that has meant a Fall Fun Zone and Pumpkin Patch running from late September through Halloween, with slides, hay bales, a corn crib, gem mining at Prospectors Point, and food from vendors like Stonies Brats and Dogs. The same physical spot that spends six months selling produce spends October selling pumpkins and straw-bale entertainment to families, a pivot that repeats every year and that longtime residents plan their weekends around without necessarily linking the two seasons together.
Layered on top of that is Greentree, Kirkwood's marquee weekend, running Friday through Sunday, September 18 through 20. This is the 65th year of a festival that started in 1961 as the city's response to a run of drought and Dutch elm disease that had wiped out much of its tree canopy. What began as a replanting effort became Kirkwood Park's biggest weekend, with a parade that starts near Kirkwood High School along Dougherty Ferry, continues along Peeke, turns south on Kirkwood Road, and finishes west on Argonne into the park itself. This year's festival is tied to the America 250 theme, and the city has been clear that dogs, bikes, and rollerblades aren't allowed in the parade area, which catches out-of-towners off guard more often than residents.
Three miles up Big Bend, a different market keeps its own hours
Webster Groves doesn't run its farmers market through city hall. It sits at Oakwood and Big Bend, inside the Old Orchard Business District, and for most of the year it operates as a normal weekly market without the fanfare Kirkwood's gets. The one night it does get dressed up is tied to the Old Orchard Fall Festival, when the market shifts into an evening format with regional farmers, makers, food trucks, and drink vendors that in years past have included names like Fil-Am Fusion, Off Elm, Do More Good Coffee, and Crispy Sips.
This year's Old Orchard Fall Festival runs Saturday, October 24 through Sunday, October 25, based at 8130 Big Bend Boulevard. The festival's own event listing describes a petting zoo, live music, food trucks, and a vendor market spread through the neighborhood rather than confined to one park, and in past years the weekend has also included trick-or-treating at participating businesses. It uses the whole business district as its venue instead of a single green space, which changes how it feels to walk through compared with a park-anchored event like Greentree.
Here's how the two towns' anchor events actually compare:
| Kirkwood | Webster Groves | |
|---|---|---|
| Anchor market | Kirkwood Farmers' Market, 150 E. Argonne Dr. | Webster Groves Farmers Market, Oakwood & Big Bend |
| Founded | 1976 (50th season in 2026) | Runs through Old Orchard Business District |
| Fall pivot | Fall Fun Zone & Pumpkin Patch, late Sept. through Halloween | One evening Night Market, tied to Fall Festival |
| Signature weekend | Greentree Festival, Sept. 18–20 (65th year) | Old Orchard Fall Festival, Oct. 24–25 |
| Venue | Kirkwood Park, a single 92-acre site | Spread across Big Bend business corridor |
The one point where these two separate calendars tend to overlap is late October. If the Pumpkin Patch follows its usual run through Halloween, it will still be open the same weekend Webster Groves is hosting its Fall Festival, which is the closest thing Webster-Kirkwood has to a shared season.
What's actually different to eat this year
The business notes column that tracks this stretch of Manchester and Lockwood has logged a fair amount of turnover over the past year, and it reads less like decline than like a corridor shuffling its footprint. DD Mau, the Vietnamese spot known for its rare steak pho, closed its original Allen Avenue location and reopened at a larger space at 8169 Big Bend Blvd, the former home of Weber's Front Row. Katie's Pizza & Pasta in Rock Hill is following a similar path, moving from 9568 Manchester Road into a bigger space at 9500 Manchester in the same plaza, a relocation planned for early spring 2026. Kilwins moved into the former Jet's Pizza spot at 234 W. Lockwood Ave. right before the holidays, and Madrina, the Italian restaurant in Webster Groves, was named Missouri's top destination for authentic Italian dining in a 2026 national travel roundup.
Not every change was an expansion. Session Taco closed its Downtown Kirkwood location on Jefferson in January, Robust Bistro & Wine Bar on Lockwood wound down with its owners in talks to sell, and Global Brew Tap House in Rock Hill closed in March. Two new studios filled out the wellness side of the corridor instead: Blackbird Yoga opened on Big Bend, and it joined OM Old Orchard for a joint yoga booth at last year's Fall Festival, a pairing likely to repeat given how the two studios already work together.
A weekend-by-weekend way to plan the stretch
For residents trying to sequence the next two months without missing anything on either side of town, the run looks roughly like this:
- Now through late September: Kirkwood Farmers' Market closes out its 50th season on its normal Argonne Drive schedule.
- September 18-20: Greentree Festival, Kirkwood Park, running Friday evening into Sunday, with the parade and folklife and crafts booths spread across the weekend.
- Late September: The Summit's Fall Fun Zone and Pumpkin Patch opens at the Kirkwood market site, typically running into Halloween.
- October 24-25: Old Orchard Fall Festival along Big Bend, Webster Groves, with the farmers market's evening Night Market historically part of the weekend.
- Late October: If the Pumpkin Patch is still running, this is the one stretch when both towns' fall attractions overlap.
None of this requires choosing a side. It just means knowing that a Saturday spent at the Pumpkin Patch and a Saturday spent at Old Orchard are two different traditions, run by two different business districts, that happen to land in the same few weeks.
If you're weighing a move between these two downtowns, or just trying to figure out which side of Big Bend fits how you actually spend your weekends, that's the kind of texture that doesn't show up on a listing sheet. Meggin Martin works both sides of this corridor and can walk you through what daily life looks like on each end of it. Let's connect.
