Portola Valley almost seems like it could be part of Marin County, with its long twisting roads that pass redwood and oak trees, tennis and swimming clubs, expensive houses and horse stables.

But this wealthy San Mateo County town of 4,000 is very much a part of Silicon Valley. One of its main roads, Portola Road, leads to Sand Hill Road, home of the valley’s famed venture capital firms.

Located west of Interstate Highway 280, Portola Valley is a nice place for a country drive. Also, there’s hiking in the Windy Hill Open Space Preserve’s 1,414 acres (as well as parking areas on Portola Road) and horses and riding at Spring Down Equestrian Center.

Portola Valley Town Center has tennis and pickleball, and its athletic fields are framed against the Santa Cruz Mountains next to a library and civic buildings.

Portola Valley Town Center has athletic fields and tennis and pickleball courts. (Courtesy Larry Sokoloff)

Portola Valley’s biggest draw is undoubtedly the Alpine Inn, a 250-seat beer garden and restaurant and bar established in 1852. Having changed names multiple times through the decades, it’s been a California historical landmark since 1969 and on the National Register of Historic Places since 1973. Today it’s also known as Rossotti’s and Zott’s. What you call it tells folks how long you’ve been in these parts.  

By whatever name, this roadhouse is a South Bay institution. You can sit outside under an umbrella or in a smaller bar area while sipping a beer or eating a pizza or burger in a kid- and dog-friendly setting. You’ll probably hear Los Trancos Creek, which flows along one side of the property. Large TVs are on to watch sporting events. But be prepared to wait for a table on busy nights.

There’s an onslaught of Stanford University sports memorabilia; the inn is located five miles from the Farm, and it’s a hangout for Stanford alums, students and employees. But it’s also a popular place for hikers and cyclists or tech workers on their way home.  

The town and adjacent parts of Santa Clara County have an extensive trail system. While you’re waiting for your table, you might consider going for a short hike. Palo Alto’s Pearson-Arastradero Preserve is a half mile away.

The historic Alpine Inn in Portola Valley even offers horse parking. (Courtesy Larry Sokoloff)

Note: Alping Inn has lots of parking, including carpool, bicycle and even horse parking. Or park along Arastradero Road and walk over.

The operation at the Alpine Inn was upgraded under new owners in 2019, and it’s now much larger, with a more extensive menu. While the indoor Alpine Inn historic tavern seats 50, there’s a more recent tie to history relevant to today’s Silicon Valley. A plaque outside the tavern marks the beginning of the internet age. In August 1976, an electronic message from a computer set up on a picnic table here was sent by a team from nearby SRI International to Boston.  

Alpine Inn isn’t the only Portola Valley eatery. Other area restaurants, mostly offering outdoor seating, include Parkside Grille, Portola Kitchen, Amigos Grill and Old Port Lobster Shack.