Kirkwood's Greentree Festival Turns 65 This Weekend. It's Not Even the Oldest Anniversary Downtown Is Celebrating.

Walk down Argonne this week and you'll pass banners for a festival turning 65, a market marking 50 years in the same two blocks, and a storefront getting ready to open its doors for the first time. None of these are connected on paper. They don't share an organizer, a budget, or a planning committee. But they're all happening within about 600 feet of each other, inside the same three-week window, and if you only show up for the one everybody's talking about, you'll miss the other two entirely.

That's the thing about downtown Kirkwood this fall. The headline event isn't the whole story. It's just the loudest one.

Three anniversaries, one footprint

Here's what's actually converging on Kirkwood Park, the train station corridor, and the stretch of Argonne and Monroe between them this month: the Greentree Festival hits its 65th year this weekend. The Kirkwood Farmers' Market quietly crosses 50 years in the same stretch of days. And a new restaurant tied to one of Clayton's better-known café owners is set to open directly across from the Kirkwood Performing Arts Center before September is out.

None of these needed to line up. The festival dates back to 1961, when the city responded to a wave of tree loss from drought and Dutch elm disease by planning a celebration under the trees that survived. The market was founded fifteen years later, in 1976, as Kirkwood's bicentennial project. The restaurant opening has nothing to do with either anniversary. It's simply that downtown Kirkwood has spent the last few years building enough density around its train station and arts center that new businesses now land in the same six blocks as the city's oldest traditions, instead of scattering out toward the highway.

If you live here, that's worth knowing not because it changes your weekend plans, but because it explains why downtown has started to feel different even on an ordinary Tuesday.

This weekend: the 65th Greentree Festival

Greentree runs Friday, September 18 through Sunday, September 20 at Kirkwood Park, and this year carries a patriotic theme tied to the country's 250th anniversary. The City of Kirkwood's parade route starts near Kirkwood High School on Dougherty Ferry, continues along Peeke, turns south on Kirkwood Road, and heads west on Argonne toward the park, so if you're planning to watch rather than march, staking out a spot along that stretch beats fighting the crowd at the park gates.

Grand marshal duty this year goes to Fire Chief Jim Silvernail and Police Captain Doug Raymond, a choice the city tied explicitly to both the America 250 theme and the 25th anniversary of September 11. Silvernail told the Webster-Kirkwood Times he sees the role as representing the department rather than himself, "not only the people that are here now, but the people who were here before me and the people who will come after me." Raymond, who has 34 years with the city, has described Kirkwood as a "big, small town" where the everyday relationships matter more than any single event.

The festival itself runs on the same bones it's had for decades: two music stages, an arts and crafts fair, food booths, a kids' zone, and a wine garden, all inside Kirkwood Park's 92 acres. That's the same park that holds Walker Lake, the Kirkwood Community Center, the Robert G. Reim Theater, and the city's aquatic center and ice arena, which is part of why Greentree has never needed to expand its footprint. The infrastructure was already sized for it. Admission is free, as it has been every year since 1961.

The market that's been here longer than most of the businesses around it

Here's the anniversary most people walking through downtown this month won't clock. The Kirkwood Farmers' Market, at 150 E. Argonne on the corner of Argonne and Taylor, is marking 50 years in 2026. It was founded by the City of Kirkwood as a bicentennial project, and it's still owned by the city today, administered through the Downtown Kirkwood Special Business District, in a business district that now counts more than 300 local storefronts around it.

The market's regular season runs through the end of September, and on Friday, September 25, the district is hosting a Night Market on Argonne from 4:30 to 8:00 p.m., a later evening format built around live music and local vendors rather than the usual Saturday-morning produce run.

After that, the market doesn't close. It hands off. The Summit All Seasons Market takes over the same footprint for its fall program, which means more than 30 varieties of pumpkins, mums, seasonal décor, over 150 kinds of candy and treats, and a Kids Fun Zone that opens alongside what the Summit calls its Great Pumpkin Patch. It's the same physical spot, the same fifty-year-old civic institution, just wearing its October coat. If you've only ever thought of the market as a summer produce stop, the fall version is worth a walk-through on its own.

What's moving into the same six blocks

While the market and the festival are both marking round-number anniversaries, the newest addition to downtown is opening for the first time. Ivy on Monroe, the Kirkwood expansion of Clayton's Ivy Cafe, is projected to open in late September at 132 E. Monroe, on the ground floor of the new Aria condominium building, a five-story, 42-unit development directly across from the Kirkwood Performing Arts Center.

Owner Julie Blackerby went before the Kirkwood City Council in August to secure a special use permit for outdoor dining and occasional live entertainment, requesting seating for up to 50 people on the patio in addition to indoor tables. Hours are set at 7 a.m. to 10 p.m. Monday through Saturday and 7 a.m. to 8 p.m. on Sunday, matching the original Clayton location's daytime café hours before easing into an evening wine bar service. Kirkwood will launch with the same menu as Clayton and add a Sunday dinner service the original doesn't currently offer.

The location matters more than it might seem. KPAC has been drawing evening foot traffic to that stretch of Monroe for a few seasons now, and a full-service restaurant opening directly across the street means the theater's audience has somewhere to land before or after a show without leaving the block. It's a small detail, but it's the kind of small detail that turns a two-hour outing into a full evening, and it's happening at the same time the city's other two institutions are marking half a century and 65 years, respectively, a few hundred feet away.

What this means if you're the one who lives here

None of this requires a decision from you. Nobody's asking you to pick a side between the festival, the market, or the new restaurant. But if you've lived in Kirkwood long enough to think of Greentree as the one weekend downtown gets busy, this fall is a good moment to notice that the crowded weekend isn't really the whole pattern. It's the visible peak of a much longer, quieter build that's been happening on the same blocks since a market started in 1976 and a tree-planting festival started in 1961, both of which are still running, both of which just picked up a new neighbor.

Go to the parade. Walk the Night Market on the 25th. And when Ivy on Monroe opens its doors across from KPAC later this month, that's worth a look too, not because it's new, but because of exactly where it's landing.

If you're already part of this neighborhood and want to talk about what any of this means for your street, your block, or your home's place in it, Stacy Deutschmann is always happy to catch up. Let's connect, whether that's for a market update or just a conversation about what's changing around you.