Santa Rosa's Summer 2026: The Rooms That Came Back, and the Week They Anchor
July 23, 2026
July 23, 2026
Something quiet happened between last summer and this one. Three of the restaurant rooms Santa Rosa lost between 2022 and 2025 have either reopened under new operators or are close to it, and the week between the Wednesday Night Market and Sunday's concert at Juilliard Park now runs through addresses that were dark a year ago.
If you already live here, the practical question isn't what's new on a map. It's whether the season actually works differently now. The short answer is yes, and the change is concentrated in three corridors: the ridge above Annadel, Montgomery Drive, and Guerneville Road west of downtown.
The Villa closed in 2022 after Gaspare Bernardo retired, and the building sat empty for roughly three years above Annadel State Park. This spring it reopened as The Junction, a project from Liz and Dez Fiedler with Jeff Krupman of San Francisco's Pizza Hacker, the same trio behind the original Junction in Mill Valley.
The Santa Rosa version isn't a copy. It's a full-bar location built around a 4,000-square-foot beer garden with a play area and live-music stage, a 150-seat dining room, a 30-tap draft program, and an on-site bottle shop. The interior was reworked so glass walls put the view forward rather than treating it as background. Krupman's Pizza Hacker menu of blistered large-format pies carries over, joined by salads, wings, and fried chicken.
For a resident, the useful detail is that this is now a family-scaled group room again, not a special-occasion Italian dining room. That's a category Santa Rosa has been thin on since 2022. The Junction has also started hosting mid-week concerts on the beer garden stage. Hot Buttered Rum and Tea Leaf Green played the space in mid-July.
On Montgomery Drive, the former Lepe's space at 4323 has reopened as Parkside Eats, run by Hayley Cutri and chef Efrain Balmes. The two closed their Sonoma Eats restaurant in Agua Caliente after the building went up for sale and moved the concept north. The menu blends Mexican-influenced dishes like quesabirria, birria hash, and al pastor tacos with California-style burgers, poke nachos, and fish tacos, served across breakfast, lunch, dinner, and weekend brunch.
A few minutes away at 909 Village Court, Olives and Agave has taken over the former Cascabel space in Montgomery Village with a tapas menu drawing on Spain and the Middle East. Cascabel had closed quietly in May 2025, and the corner had been dead ever since.
Two everyday-use rooms opening within a mile of each other, on a stretch that had been losing operators, is the kind of shift that changes where you actually go on a Tuesday.
Walter Hansel Wine & Bistro closed on Guerneville Road in west Santa Rosa in August 2025 after twelve years, with owner Stephen Hansel citing rising food costs and declining foot traffic. The building, which dates to 1944 and started life as a chicken coop before cycling through the Big Oak Chicken Shack, the Spaghetti Factory, Willowside Café, and Zazu Kitchen + Farm, is scheduled to reopen in late summer as Owl & The Vine.
The new operators are Lawrence and Stephanie Bondulich from Manhattan's Upper West Side, where they run Bin 71, a 21-year-old Italian enoteca-style wine bar with more than 100 wines by the bottle and about 30 by the glass, along with a cocktail bar called The Owl's Tail. This will be their first Sonoma County project. Menu details aren't public yet, but the format they're bringing over is wine bar and taproom, not full white-tablecloth dining, which fits the roadside building better than the previous concept did.
The other reason the week reads differently in 2026 is that the free and low-cost concert calendar is unusually stacked. Three long-running series overlap through August, and downtown's Wednesday market runs alongside them.
| Series | When | Where | Cost |
|---|---|---|---|
| Wednesday Night Market | Wednesdays through Aug 12 | Old Courthouse Square | Free |
| Live at Juilliard | Sundays 5–7 p.m. | Juilliard Park | Free |
| KRSH Backyard Concerts | Select Thursdays and Fridays, 6–8 p.m. | 3565 Standish Ave. and Old Courthouse Square | Free |
| Fridays at the Hood | Fridays 7–9 p.m. through Aug 21 | Hood Mansion | Ticketed |
Fridays at the Hood is the one worth planning around if you haven't been. The remaining bookings lean into roots genres, with Lavay Smith and Her Red Hot Skillet Lickers on July 24, the Anthony Paule Soul Orchestra on August 7, and MOMOTOMBO SF closing the series on August 21. Gates open at 6 p.m., and the hillside seating fills earlier than most visitors expect. Live at Juilliard is now in its 31st year, which puts it in the same tenure category as the fair.
The Sonoma County Fair runs August 7 through 16 this year at the fairgrounds on Bennett Valley Road. For most residents the useful piece of information isn't the fair itself, which you already know how to use, but the traffic and parking spillover it produces on the surrounding blocks. The fair's ten-day window overlaps directly with the final Wednesday Night Market (August 12), the last two Fridays at the Hood, and the Backyard Concert schedule.
If you're trying to see one of the Hood Mansion shows during fair week, give yourself more time than you think. The routes east of downtown thicken noticeably in the late afternoon during the fair's run, especially on the weekend nights.
Later this year the rebuilt Cricklewood site is scheduled to open as Hapa's on the Mainland, a Hawaiian concept from Ann and Dennis Tussey of Sweet T's in Windsor along with pit master George Ah Chin. Cricklewood was on that stretch of Old Redwood Highway for decades before a fire took the building. A steakhouse-adjacent room with indoor dining is a different animal than the taproom or taco format the rest of this summer's openings share, and it's the closer worth watching between now and the end of the year. Downtown, Café Carrusel opened on June 23 for brunch, and the new Redwood Gospel Baking Company café has become a workable weekday coffee stop with a legitimate almond croissant.
Santa Rosa lost a lot of restaurant rooms between the 2017 fires and the 2022 staffing crunch, and the ones that came back before this year mostly replaced casual with more casual. What's different about summer 2026 is that operators are willing to take on buildings with size and history again. The Junction's 150-seat room, the Guerneville Road roadhouse, and the Cricklewood rebuild are all bets that a mid-size destination room can work here at 2026 costs. Some of the operators making those bets, like the Bondulichs, are underwriting rent that Bay Area chefs describe as noticeably softer than San Francisco.
For a resident, the practical takeaway is that the week has more shape than it did last summer. There's a hilltop option that works for a group with kids, a Montgomery Drive corner that works on a weeknight, a Guerneville Road wine bar coming in a few weeks, and four separate free or low-cost music series overlapping through late August. The Wednesday Night Market wraps on August 12. Fridays at the Hood wraps on August 21. If you were planning to use the season, the next six weeks are when it's densest.
If you're weighing what this kind of neighborhood change means for your own move, whether that's a first home near Montgomery Drive or a hillside property closer to Annadel, Alexander Goodman is happy to walk through the specifics of what Santa Rosa actually feels like block by block. Let's Connect.
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