In 2003, James Smallwood moved into the WireWorks Lofts in Lafayette Square. He was working for AT&T's corporate office and became a regular at 33 Wine Shop & Bar on Park Avenue. In 2013 he bought the place. Years later he married his co-owner, Jessica Spitzer, at the bar, in May 2025. On August 28, 2026, he served his last night there.
Four weeks earlier, 33's longtime next-door neighbor, Baileys' Chocolate Bar, closed after 22 years. That left two dark storefronts side by side at 1913 and 1915 Park Avenue. The new places opening in and around the neighborhood are a different kind of business. A garden market that opens at 6 a.m. A diner whose happy hour ends at 10:30 in the morning. A bread bakery big enough to supply a citywide operation. Since August, the new money has gone into daytime food, and the reasons trace back to what it costs to keep a bar open at night.
The 1900 block of Park Avenue, door by door
The block where both closures happened is still busy. Here is what the most recent coverage and the businesses' own pages show for each address:
- 1913 Park Avenue. 33 Wine Shop & Bar closed August 28 after 25 years. St. Louis Magazine's September roundup logged the closure without naming a replacement.
- 1915 Park Avenue. Baileys' Chocolate Bar closed after service on August 1. In July, Dave Bailey said the group hoped to host private events in the space for a short time, and that someone could buy, lease, or take it over. No incoming tenant was named.
- 1919 Park Avenue. Park Avenue Coffee is open and posts weekly hours.
- 1923 Park Avenue. Polite Society serves dinner seven nights a week, plus brunch, and takes reservations.
A few blocks west, Square One Brewery & Distillery is still serving at 1727 Park Avenue. Eleven Eleven Mississippi is still at 1111 Mississippi and offers carryout ordering. Dinner is still easy to find in Lafayette Square. What the block lost was a dessert-and-drinks counter and a wine bar, two businesses that made their money on lingering evenings out.
What a $24,000 insurance bill says about evening hours
Both closures came down to cost. Baileys Restaurants called its decision a company restructuring. Dave and Kara Bailey said closing the Chocolate Bar and Baileys' Range would free up resources for Rooster and the catering business. They pointed to rising food costs, interest rates, labor issues, and other financial obligations.
At 33, the numbers were blunter. Smallwood told St. Louis Magazine that the bar's business insurance went from $6,000 a year in 2013 to $24,000 a year in 2026, even though he never filed a claim. Health insurance costs had also soared, the lease was up for renewal this fall, and people were going out less and drinking less when they did. "We were dealing with death by a thousand cuts," he said.
The insurance number matters because it hits only one kind of business. A policy that quadruples simply because a place serves alcohol puts no pressure on a coffee counter or a bakery. A neighborhood business owner looking at this block in 2026 faces very different math for an all-day cafe than for a bar that does most of its sales after dark.
What closed was more than a shop. As of January 2025, 33 carried 900 labels and 4,000 bottles. Its three-tier wine club had 133 members, and it ran regular wine classes. Spitzer put the loss this way:
"People think a place like this is an institution, that it will always be there. But if you don't support it, it's gone, and then you have nowhere to go."
South 18th Street opens at 6 a.m.
The first new business to open went into South 18th Street, not Park Avenue. Picky Cafe & Market opened at 1410 S. 18th St. on Monday, August 31. It is Erin Budde's urban garden, market, and cafe, created with her sister, Bethany Budde Cohen. The menu changes with the seasons and covers breakfast and lunch, baked goods, coffee, smoothies, fresh produce, and grab-and-go items. Picky's own page lists hours of 6 a.m. to 6 p.m., Tuesday through Sunday. St. Louis Magazine's opening story printed a seven-day schedule, so check before planning a Monday visit.
Picky didn't come from nowhere. Budde Cohen has run SqWires at 1415 S. 18th St., directly across the street, for 25 years. So the newest business on the street comes from one of its longest-running operators, who is expanding into the early-morning hours.
A few doors south, at 1463 S. 18th St., Kingside Diner is preparing its fifth location in the former Rosé by Peno space. The diner is operated by Aaron Teitelbaum's The 5 Senses LLC. The plan calls for full table service, coffee, and a bar. It will serve seven days a week, with breakfast and lunch first and evening hours possibly added later. The bar comes with an early happy hour that runs until 10:30 a.m. Even the drinking at the new diner is scheduled around the morning.
Kingside was announced for early October. As of October 4, its Lafayette Square page still shows a progress gallery of the patio, the sidewalk window, and an exposed-brick interior. It invites neighbors to "watch our progress" but gives no opening date. If you're watching the storefront for paper to come down, it should be soon. The diner itself has not yet announced a date.
The bread on Russell started at the wine bar on Park
The biggest of the incoming projects sits just south, at 1854 Russell Blvd. in McKinley Heights, in the space that used to be Gather. Union Loafers is building a combined bread bakery and cafe there. It is meant to quadruple the company's bread capacity. About two-thirds of the 4,600 square feet will go to baking, with the rest set aside for the cafe. The original Union Loafers is still at 1629 Tower Grove Avenue in Botanical Heights.
KSDK reported a target of late September or early October. St. Louis Public Radio's October 1 roundup of September openings did not include it, and none of the coverage gave a specific opening date or cafe hours.
This bakery has a link to the wine bar that just closed. Union Loafers co-founders Sean Netzer and Ted Wilson both worked at 33 Wine Shop & Bar, and so did longtime general manager Steve Russell. Two master sommeliers, Andrey Ivanov and Brandon Kerne, also learned their trade there. Smallwood and Spitzer count those people as part of 33's legacy. One of the most-watched openings near the neighborhood this fall comes from people who once poured wine on Park Avenue. Their new business is built around bread, and bread doesn't carry a $24,000 liquor-liability premium.
A butcher counter by order form
Just outside the neighborhood, at the Centennial Malt House, 2017 Chouteau Ave., Sam Rice is launching The Malt House Butcher. It is a custom-order business that starts with sides and quarters of local beef. It was announced for early September. The website works from an order form, with pickup or delivery, and posts no walk-in hours. It fits the pattern of the other openings. Like Picky's produce shelves and the bread coming to Russell, it sells food people take home, without the overhead of a bar.
What is open now, and what is still coming
For a resident planning the next few weeks, here is the current status of each place:
- Open now. Picky Cafe & Market at 1410 S. 18th St., 6 a.m. to 6 p.m. on the days its own page lists. SqWires across the street at 1415 S. 18th St. Park Avenue Coffee at 1919 Park. Polite Society at 1923 Park. Square One at 1727 Park. Eleven Eleven Mississippi at 1111 Mississippi.
- Announced for early October, not yet confirmed open. Kingside Diner at 1463 S. 18th St. and Union Loafers Bakehouse and Cafe at 1854 Russell.
- Ordering by form. The Malt House Butcher at 2017 Chouteau, custom orders for pickup or delivery.
- Waiting on news. 1913 and 1915 Park Avenue, where the summer closure coverage named no incoming tenant.
Whatever comes next at 1913 and 1915 Park Avenue is the next thing to watch. A cafe, a bakery outpost, or another all-day concept moving in would confirm that the neighborhood's business district now runs on daytime trade. An evening tenant signing on would show that someone has found a way to make the bar math work at today's insurance prices.
If you own a home near Park Avenue or South 18th Street and wonder how changes like these on the commercial blocks show up in what nearby homes are worth, Daryl Holland is glad to talk it through with you, calmly and with no pressure. Schedule a free consultation, and we can look at your street together.
This article is general information, not legal, tax or financial advice. Consult a qualified professional about your situation.
