Tonight, Courthouse Square is showing "So I Married an Axe Murderer" as part of Summer on the Square, the same free Monday movie series the city has run for years. Two days from now, the Wednesday Night Market sets up on Fourth Street for one of its last sessions of the season. Down at the fairgrounds, the Sonoma County Fair is in the middle of its ten-day run, which wraps August 16.
None of that is new. Santa Rosa has run some version of this downtown calendar every summer for a long time.
What's different this year is what's happening on the two sides of town that downtown usually has to carry alone. The hilltop above Montgomery Drive, dark for more than three years, reopened in May. A stretch of Guerneville Road that lost its anchor restaurant last August is getting a new one before summer ends. For the first time in a while, a Santa Rosa resident deciding where to spend a Friday night has three real options within about fifteen minutes of each other, instead of one reliable option and two empty storefronts.
Three Corners, One August
| Where | What's There | Status Right Now |
|---|---|---|
| Montgomery Drive, east side | The Junction, Parkside Eats | Both open and running full weekly hours |
| Guerneville Road, west side | Owl & The Vine | Under construction, targeting a late-summer opening |
| Courthouse Square, downtown | Wednesday Night Market, Summer on the Square | Wrapping their season the same week as the county fair |
The Hilltop That Sat Dark for Three Years
The building above Montgomery Drive has been a Santa Rosa landmark since 1962, when it opened as The Hilltopper, a mid-century spot known for continental dishes like lobster thermidor served for under four dollars. Gaspare Bernardo took it over in 1976 and ran it as The Villa, an Italian restaurant with a tableside Caesar salad, for nearly fifty years before he retired and closed the doors in 2022.
The building sat empty for more than three years, slowly wearing down above one of the city's busier commuter roads, before Liz and Dez Fiedler and business partner Jimmy Simpson bought the property. The trio had already built a following with the original Junction in Mill Valley, a beer-and-pizza spot that opened in 2020 on a similarly distressed piece of land at the edge of the Golden Gate National Recreation Area. Their Santa Rosa version opened May 11, 2026, with a 150-seat dining room, a 30-tap draft list, and roughly 4,000 square feet of outdoor beer garden with fire pits and a play structure for kids. The old half-moon front doors and vaulted ceilings stayed. So did the roadside sign that generations of diners used to spot the turnoff.
Bernardo showed up for the reopening. According to Sonoma Magazine, he sat with his family over pizza and watched the space he ran for four decades come back to life. Co-owner Liz Fiedler put it simply:
"Everyone who comes by has a story to tell us. People remember this place."
The Junction isn't the only thing that's changed on that stretch of road. A few blocks away at 4323 Montgomery Drive, Parkside Eats opened in April 2026 in the former Lepe's space, serving birria hash, burgers, and fish tacos for breakfast through weekend brunch. Sonoma Magazine reported that the restaurant filled up almost immediately, with no formal opening fanfare needed. Montgomery Drive spent three years as a road you drove past. This summer it's a road people are driving to.
Guerneville Road's Faster, Quieter Comeback
On the opposite side of the city, a different kind of reopening is underway, on a very different timeline.
Walter Hansel Wine & Bistro closed in August 2025 after twelve years on Guerneville Road. Owner Stephen Hansel cited rising food costs and declining foot traffic, a combination that has closed more than one long-running Sonoma County restaurant in the past few years. Unlike the Villa's multi-year vacancy, this space sat empty for closer to a year before new owners stepped in.
The new owners are Lawrence and Stephanie Bondulich, a husband-and-wife team from New York who currently run Bin 71, an Italian enoteca-style wine bar on Manhattan's Upper West Side now in its twenty-first year with more than 100 wines by the bottle. They also own The Owl's Tail, a cocktail bar in the same neighborhood. Their new project, Owl & The Vine, is targeted to open in late summer 2026 and marks their first venture in Sonoma County.
The building itself has been through more changes than most people driving past it realize. It went up in 1944 as a chicken coop, then became a restaurant known as Big Oak Chicken Shack in the late 1940s. Over the following decades it cycled through the Spaghetti Factory, the Country Western Bull Rider Saloon, Willowside Café, and most recently Zazu Kitchen + Farm. Details on Owl & The Vine's menu haven't been released yet, but the pattern on that stretch of Guerneville Road has been consistent for eighty years: something new always moves in.
Downtown Doesn't Need Reinventing, It Just Needs the Timing to Line Up
Courthouse Square isn't doing anything unusual this year. The Wednesday Night Market has run from May 13 through August 12, the same as most summers, with artisan vendors, farm produce, and live music filling the square on Wednesday evenings. Summer on the Square keeps its Monday movie nights going with pre-show entertainment and food from local vendors. Tonight's screening is part of that same recurring series.
What makes this particular week worth noting is where it lands on the calendar. The market and the movie series are both closing out their season during the exact same stretch as the Sonoma County Fair, which runs August 7 through 16 this year. For a few days, downtown's reliable, familiar programming and the fairgrounds' once-a-year carnival rides, agricultural exhibits, and wine country horse racing are both drawing people at once, instead of the fair having the week to itself the way it usually does.
If you want one more reason to stay downtown after the fair packs up, Historic Railroad Square hosts its ninth annual free music festival on September 28, with four stages and more than a dozen local acts.
What This Actually Means If You Live Here
In most recent summers, choosing where to spend an evening in Santa Rosa meant choosing downtown, because downtown was the only part of the city reliably doing something. The hilltop was a boarded-up building. The Guerneville Road corridor had one fewer restaurant than it used to. This year, for the first time since 2022, all three zones have something worth the drive in the same season.
A realistic August week might look like this: Monday night downtown for the movie on the square, a Wednesday stop at the night market for dinner from a food vendor, and a Friday or Saturday drive up Montgomery Drive to catch a sunset from The Junction's patio, with a view toward Trione-Annadel State Park. If you're headed that way, know that parking is still the one wrinkle. Sonoma Magazine's writeup noted cars lining the steep driveway during busy hours, with an overflow lot nearby for anyone willing to walk up.
By late August, keep an eye on Guerneville Road for signage. Owl & The Vine hasn't announced an exact opening date, but a summer 2026 target means the fourth corner of this story could be open before the season ends.
None of this changes what Santa Rosa is. It changes what a normal week here looks like right now, which is the kind of thing you only notice if you've been paying attention to more than one side of the city at a time.
If you're weighing a move to Santa Rosa, or you already live here and know someone who's curious about the market, Pat Kelly Real Estate has spent years tracking these neighborhoods block by block. Reach out anytime you have a question about what a particular street or corridor is actually like to live on.
