Things to Do in Portola Valley This August

Thursday evening at the Town Center, the farmers market tables are folding up and a different crowd is spreading blankets on the Performance Lawn by the library. Two miles up Alpine Road, a separate crowd is filing through a vineyard gate with wine glasses in hand, checking tickets they bought back in April. Both are part of Portola Valley's summer calendar, organized by different groups.

These venues and events are organized in different ways: some involve the town, while others are run by private businesses, a nonprofit, or a regional agency. Portola Valley does not have a city recreation department.

Two Thursdays, Two Owners

The Portola Valley Summer Concert Series has been running since 2010, funded by the town, staged on Thursday nights from 5:30 to 8 p.m. on the Performance Lawn right after the farmers market wraps. Food trucks stick around from the market, and the crowd brings its own blankets and picnic baskets. This year's lineup has already brought Fog City Swampers doing classic rock covers and Freddy Clarke & Wobbly World mixing jazz with Afro-Cuban and funk, with Bundy Browne & Guitar Gypsy covering Americana and R&B still to come in September. Elsewhere in the season's slate, Dennis Johnson & The Revelators bring their blues-rooted live show, and Petty Rocks, a Tom Petty tribute act, plays a set that means a little more locally: the band's bassist, Andy Hewett, lives in town.

The town pays for it, but the fundraising and coordination now run through the PV Palooza Foundation, the same nonprofit that throws the town's end-of-summer festival.

Two miles away, SummerJazz at Portola Vineyards runs on a completely different model. Tickets for the 2026 season went on sale April 1, and the vineyard warns upfront that concerts usually sell out quickly. The opening show did exactly that: Brazilian jazz vocalist Claudia Villela, whom Jazz Times once called "a Brazilian-born genius with a blistering voice," played to a sold-out house on June 14 with a waitlist for anyone who missed it. The season continued with multi-instrumentalist Steven Lugerner and Grammy-nominated composer Marcos Silva. Gates open at 5 p.m. and music runs 6 to 7:30, with admission including a tasting of the vineyard's own wines alongside a bring-your-own picnic.

Same town, same season, two entirely different ownership structures. If you've wondered why one night feels like a neighborhood potluck and the other feels like a reservation you had to plan around, this is why.

Rossotti's Alpine Inn and Its Beer Garden

Rossotti's Alpine Inn sits on the banks of Los Trancos Creek and has operated continuously since 1852, making it the second oldest tavern in California. It has worn a lot of names over the decades, Casa de Tableta, The Wunder, Schenkel's Picnic Park, Zott's, but it has never once belonged to the town. When the property came up for sale in 2018, three local families, Deke and Lori Hunter, Fred and Stephanie Harman, and Jim Kohlberg, bought it and brought in restaurateur Greg St. Claire to run the restoration.

"The sheer joy on customers' faces and a packed beer garden make it all worthwhile."

That's St. Claire describing the reopening to Palo Alto Online, and it captures why the place still functions as the town's unofficial living room even though it has always been privately owned. The beer garden and tavern currently run Tuesday through Thursday from 11:30 a.m. to 9 p.m., Friday until 9:30, and weekends from 10:30 a.m., closed Mondays. It is also, almost incidentally, a footnote in internet history: in 1976, SRI researchers sent the first two-network transmission between a van parked at the Alpine Inn and UCLA over ARPANET, using a picnic table as their workstation.

The Trail Behind the Library Is Managed by a Regional District

Windy Hill Open Space Preserve, the 1,132-acre stretch of hillside that most Portola Valley residents treat as a backyard, is managed by the Midpeninsula Regional Open Space District, a special district that covers land across San Mateo and Santa Clara counties.

That matters for anyone deciding how to spend a Saturday morning, because the preserve offers two genuinely different experiences from the same Portola Road trailhead:

• Sausal Pond Loop: 1.6 miles, about 200 feet of elevation gain, an easy walk past oak woodland and a pond where egrets and wood ducks show up regularly. Dogs are welcome on leash.
• Spring Ridge, Hamm's Gulch, and Lost Trail Loop: 7.2 miles, climbing through chaparral and grassland to the Windy Hill summit, with Bay views on a clear day.

The lower parking lot holds 47 spaces plus two ADA spots, and it fills fast on weekend mornings. When it does, the district's own guidance points hikers to overflow parking 0.4 miles north at the Portola Valley Town Center, reachable on foot via the Portola Trail. It's a small detail, but it's the kind of thing you only know if you've actually tried to park there on a Saturday at nine.

Roberts Market: A Family Business

Roberts Market opened its Portola Valley location in 2008 at 4420 Alpine Road, right at the corner of Alpine and Portola roads, in the building that had previously housed John's Valley Foods. The original store is in Woodside, about ten minutes away, and the family-run chain built its name on a gourmet deli, a serious wine selection, and a butcher counter that regulars mention more than almost anything else about the place. It's a family business with a second location on this corner.

PV Palooza at the Town Center

If you want the clearest single snapshot of how this all works, look at the last Saturday in August. PV Palooza, now in its fifth year, runs August 29, 2026, from 10:30 a.m. to 8:30 p.m. at the Town Center, free to attend, with a stage for touring acts, a smaller stage for local and youth bands, art exhibitors, and kids' activities. The town owns the Town Center. The PV Palooza Foundation, a 501(c)(3) nonprofit funded by local business sponsors and private donors, organizes the festival and the Thursday concert series.

What This Means If You Already Live Here

Together, these examples show how Portola Valley's summer calendar brings together the town, local businesses, a nonprofit, and a regional agency. Events range from the free Town Center concert series to ticketed SummerJazz, while Windy Hill is managed by the Midpeninsula Regional Open Space District.

If you're the kind of resident who tracks these details, whether it's who owns the trail behind your house or what your own property is actually worth in a market that keeps shifting, Anita Salas works this exact stretch of the Peninsula every day. Reach out anytime you want a straight read on the market, no pressure, no sales pitch, just a local perspective from someone who pays attention to the same details you do.