For three years, the building on the ridge above Annadel State Park sat the way empty restaurants do: blinds half drawn, weeds working through the parking lot seams, the kind of quiet that makes people slow their cars just to look. The building had been a fixture since 1962, first as the Hilltopper, then as The Villa once Gaspare Bernardo took it over in 1976. When Bernardo retired and closed it in 2022, the building sat deteriorating long enough that developers began eyeing the site, and most people assumed it was headed for demolition rather than a second life as a restaurant.
Instead, three Mill Valley restaurateurs bought it. This spring they reopened it as The Junction, same sweeping view of Annadel, an entirely different scale of ambition: a 4,000-square-foot beer garden, a 150-seat dining room, 30 taps, and a game room stocked with shuffleboard and vintage arcade machines.
A few miles down the hill, the city has spent since 2024 working toward something much smaller. Starting August 14, a single block of Ross Street closes to traffic through October 31 for food trucks on weekdays and live music on Friday and Saturday nights. The original plan was to close a stretch of Fourth Street. Downtown business owners pushed back over the effect on their own foot traffic, so the city scaled down to Ross Street, a compromise that took until June to turn into a signed agreement between the city and the Downtown Action Organization.
Both of these are real, both are happening within blocks and weeks of each other, and tonight both are sharing the calendar with a third thing: the Sonoma County Fair closes its gates for the season. Lined up together, the three tell you something worth knowing if you live here, which is that 2022 quietly took more out of Santa Rosa's routine than most people noticed at the time, and 2026 is the year some of it is finally coming back, though not in the same way twice.
A Hilltop Bought, Not Rented
The Fiedlers, Liz and Dez, lost their own home in Santa Rosa during the 2017 North Bay fires. In 2020 they opened the original Junction in Mill Valley on a lot that had been, in Liz Fiedler's words, "a partial junkyard," an old auto repair site littered with debris at the edge of the Golden Gate National Recreation Area. Working with the PizzaHacker team from San Francisco, they built a menu of blistered, large-format pies and turned a wrecked property into a pandemic-era gathering spot at the intersection of hiking and biking trails.
They brought the same collaboration north for the Santa Rosa location. Construction replaced the old floor-to-ceiling windows with glass walls that push the hilltop view forward instead of treating it as background, and pine siding now covers exterior walls that had been deteriorating for three years. The PizzaHacker lineup anchors the food, joined by new salads, wings, and fried chicken. "Everyone who comes by has a story to tell us," Fiedler said as the build-out neared completion. "People remember this place."
That's the tell. This wasn't a lease and a soft open. It was roughly two years of planning and reconstruction on a building that most people assumed was headed for demolition, funded by private operators betting the view and the memory were worth saving permanently. There's no pilot period. There's no October 31 end date. It's just there now.
Ross Street's Trial Run
Ross Street Live is a different kind of bet, smaller and explicitly temporary. Behind the Corner Store Collective, the closed block gets a stage, food trucks, seating, and public restrooms, with entertainment split among local partners: California Theater programs Friday nights, The Lost Church takes every fourth Friday, and Cooperage Brewing runs Saturdays. Local musician Ryan Woodard opened the first night on August 14 and called a dedicated run of 13 dates "an excellent starting point" for local bands who don't have many places to play outside bars and brewpubs. Josh Walden of School of Rock Santa Rosa is sending student groups, including two newly formed bands called The Okay Ultras and 945.
Longtime downtown businesses are the ones showing up to test it. Ausiello's 5th Street Bar and Grill, in its location for nearly 26 years, is participating alongside Flagship Taproom, open about a decade, and Galvan's Eatery. Downtown Action Organization board member Hali Lenox said the goal is simple: bring people back together after years when, in her words, "the gathering really slowed down."
The city itself is careful not to overpromise. A spokesperson described the pilot as a way to test expanded pedestrian space and gather feedback before anyone commits to more. If the three-month run works, backers hope it becomes a template for a permanent downtown stage. If it doesn't draw people, it quietly ends on October 31 and the block reopens to cars.
What Outlasts the Fair
Here's the detail that ties this together. Both 2022 losses that Santa Rosans have lived with for four years trace to the same year. The Villa closed in 2022, one of several closures the Press Democrat linked to that year's staffing shortages and rising food costs. That same year, Clover Sonoma discontinued its ice cream line, ending the daily free-cone giveaway that had been a Sonoma County Fair tradition for decades.
Tonight, as the fair wraps its 10-day run under this year's "Festivals, Fiestas and Fun" theme, free Clover ice cream is back for the first time since 2022. The Hall of Flowers built its "Floral Fandango" exhibition around global festival gardens, Mardi Gras next to Día de los Muertos next to a recreation of the Weifang International Kite Festival, and the fairgrounds close out with the same rodeo, grape stomp, and demolition derby that have run for generations. It's a real return, but it's a seasonal one. The ice cream comes back for these 10 days and then it's gone again until next August.
That's the pattern worth noticing. Three things that were taken from the same rough stretch of years are being restored through three different mechanisms, at three different speeds. A private capital bet rebuilt the hilltop for good. A civic pilot is testing whether a downtown block can hold onto foot traffic past a fall trial. And a seasonal tradition returns exactly on schedule, then disappears again until next year.
After Tonight's Gates Close
None of this leaves a gap once the fair ends. Ross Street Live keeps running Fridays and Saturdays through October 31, with weekday food trucks and Sunday markets in between. The Sunday farmers market at Old Courthouse Square continues through September 20, the same weekend as the Railroad Square Music Festival. SOFA's South A Street Art District keeps its monthly First Friday open studios going with no end date at all, a tradition artist Max Dubois and her neighbors built up over roughly two decades of just opening their doors. The Santa Rosa Marathon and its companion 5K run August 22, tracing Courthouse Square out along the Santa Rosa Creek Trail and Prince Memorial Greenway.
Not everything holds on. The Wednesday Night Market at Old Courthouse Square wrapped its season on August 12, four days before the fair's own close, a reminder that some things really are seasonal and end when they end. But for a town that spent 2022 through 2025 watching a beloved hilltop sit empty and a favorite fair tradition disappear, this particular week is the first time the calendar hands off cleanly from one thing to the next instead of just going quiet. The fair closes tonight. The hilltop stays open. The block party keeps testing itself through fall.
If you've been meaning to see what the fuss is about on that ridge, or want to catch Ross Street Live before it's decided whether it sticks around, the next few weekends are the ones to do it in. And if watching how Santa Rosa rebuilds its own gathering spots has you thinking about property near any of these corridors, from Railroad Square to the Bennett Valley hills, Kevin M. Properties knows this ground well enough to talk it through.
