What's New on Sonoma Plaza? Two Restaurants Reshape the Square

For months, the windows at the corner of First Street East and East Napa Street were a problem. Not because anything was wrong with them. Because people kept pressing their faces against the glass, trying to see past the paper covering, leaving smudges the staff had to wipe down every single day. The Press Democrat reported that the corner had been Maya Mexican Restaurant for more than two decades before it closed when its owners retired. Sonoma spent the better part of a year wondering what was coming next.

What came next was Dead Letter, which opened its doors this past July 16. On the opposite side of the square, a very different kind of restaurant had already opened in May, in a building with its own century of history. One of them wants you to make a reservation, settle in for the evening, and watch charcoal smoke drift past digital art on the walls. The other wants you to walk up, order a smashburger for nine dollars, and take your milkshake into the park. Both were built by chefs who already run some of the most respected restaurants in Sonoma Valley. Neither one looks anything like the restaurant that made its owners famous.

The Corner Everyone Was Watching

Dead Letter sits at 101 E. Napa St., in a building that served as one of Sonoma's early post offices between 1896 and 1910 before it spent more than twenty years as Maya. The new owners, John Toulze and Sondra Bernstein of the girl & the fig, leaned into that postal history rather than erasing it. There is a wooden postal window filled with vintage postcards. There is an Art-o-mat, the kind of vending machine that used to dispense cigarettes, now dispensing tiny five-dollar artworks. The dining rooms are dark gray and burgundy, and tall screens mounted against the stone walls quietly cycle through surreal black-and-white imagery as part of a program called PROTO.logue, curated by Bernstein herself.

The food comes off a three-level Spanish charcoal grill, with head chef Jeremy Zimmerman moving pork steaks, trout fillets, and sweet corn between levels by feel. The menu is built for the middle of the table rather than the middle of your own plate. Chicken karaage over tahini hummus runs $24. A butterflied trout in red curry runs $42. A strawberry aguachile with local rockfish runs $18. Toulze summed up the intent to the Press Democrat as simply wanting people to share, talk, and reach across the table instead of quietly working through their own dinner. Dead Letter is open Wednesday through Sunday from 5 to 9 p.m., 5 to 9:30 on Fridays and Saturdays, closed Monday and Tuesday. It is not built for a quick bite before an appointment.

Across the Square, the Opposite Bet

Smash occupies the ground floor of the Taub Family Outpost at 497 First St. West, a restored 1910 Spanish Colonial bank building that reopened in 2020 as an all-day market and restaurant complex, complete with a second-floor cocktail bar called the Beacon. The San Francisco Chronicle reported that chef Ari Weiswasser and managing partner Spencer Waite, the pair behind Glen Ellen Star and Kenwood's Stella, took it over this spring. Both of those existing restaurants are full-service, reservation-driven, farm-to-table destinations. Smash is none of those things on purpose.

Basic burgers run nine to ten dollars. Ordering is self-serve at a counter, seating is communal tables and bar stools, and there is a small patio for the days when the square isn't too busy to find a seat. The menu covers smashburgers, a Nashville hot fried chicken sandwich, tater tots, milkshakes both plain and boozy, and a vegetarian falafel burger with a gluten-free bun option. Produce comes from Glentucky Family Farm, which happens to belong to the Weiswasser family, and the bread comes from Napa Baking Company. Weiswasser told the San Francisco Chronicle the goal was something closer to "Gott's meets Shake Shack, but hyperlocal." As of late August, Smash is open daily from 11 a.m. to 8 p.m., no reservation required, and the Beacon upstairs serves the same menu alongside its cocktail list for anyone who wants the same burger with a slightly more adult setting around it.

The location matters here in a way that's easy to miss if you don't already know the square. Sonoma Plaza's central park is one of the few public spaces in California where open container alcohol is legal from 11:30 a.m. until sunset every day. Smash sits right across from it, which means a customer can order a boozy milkshake at the counter and walk it straight into the park without breaking any rule. Weiswasser and Waite had actually considered the same corner for Stella a few years earlier and passed, because a full sit-down concept didn't fit the space. Once Stella opened elsewhere in 2025, they came back to the same building with a completely different plan.

Where That Leaves the Square

Two teams. Two corners of the same small square. Neither one repeating what already made them successful elsewhere in the county.

Why the Same Kind of Chef Built the Opposite Restaurant

Here's the part that's easy to miss if you only read one of these stories in isolation. Toulze and Bernstein already have the girl & the fig, a French-leaning Plaza institution that Bernstein opened back in 1997. Weiswasser and Waite already have Glen Ellen Star and Stella, both full-service and both built around seasonal, ingredient-driven menus. None of these four people needed a second restaurant to prove they could cook. What they seem to have noticed, independently, is that the square itself had a gap neither of their existing restaurants filled.

The Plaza has never lacked for a special-occasion dinner. Cafe La Haye has anchored that corner of the market for years, El Dorado Kitchen has built its reputation on a menu that changes with the season, and now Dead Letter adds a genuinely different evening experience, with reservations recommended. What the square has lacked, according to the way both new arrivals talk about their own concepts, is a fast, inexpensive, no-reservation option for the middle of a Tuesday. In Sonoma Magazine, Weiswasser described wanting something "simpler, faster and a lot less fussy" after years of polished farm-to-table cooking. That's not a small pivot. That's a chef with a James Beard semifinalist nod choosing to build the exact opposite of what earned him that nod, on the same square where his fine-dining reputation already exists.

What It Actually Means If You Live Here

If you've lived near the Plaza for a while, the practical upshot is straightforward. There is now a place to take kids for lunch without booking ahead and without spending more than you would at a diner, and it happens to be two doors down from Valley, the natural wine bar that's been drawing its own regulars for a while. There is also, for the first time in a couple of decades, a genuinely new evening option on the square that isn't trying to be quieter or more traditional than what's already there. Dead Letter is louder, darker, and stranger than anything else within a block of it, and that seems to be exactly the point.

The corner that used to be Maya spent months as a mystery behind paper-covered windows. The corner that used to be a quiet bank-turned-market spent this spring turning into one of the loudest lunch spots in town. Both changes came from people who already had every reason to keep doing what worked. Instead they read the square differently than their own restaurants suggested they would, and built two new corners that don't compete with each other so much as they split the day between them.

If you're watching Sonoma from the outside and wondering what a town like this actually feels like day to day, this is a better answer than any single number on a listing page. The square runs on more than one clock now, morning burger counter and evening tasting menu both, and that's a texture that doesn't show up until you've walked it a few times.

If you're curious what else is shifting around Sonoma Valley this year, or you're thinking about what it would actually mean to live a short walk from all of this, I'm always happy to talk it through. Reach out to Tim McKee for a free consultation and home valuation, and let's talk about what's changing in the neighborhood you're watching.

This article is general information, not legal, tax or financial advice. Consult a qualified professional about your situation.