Day Trips and Sips: Wine Tasting, Hiking and Food in Portola Valley

Enjoy a great Portola Valley day trip adventure drinking coffee at Konditorei Cafe, hiking or mountain biking at Windy Hill Open Space Preserve, wine tasting at Neely Winery, and grabbing a bite or a beer at Alpine Inn. Ooh, game on!

By Eleanor Raab

Just off Interstate 280, there is a lovely outing full of hiking, wine and amazing food waiting for you in the town of Portola Valley. This bucolic town sits on the eastern side of the Santa Cruz Mountains, on top of a valley created by the famous San Andreas Fault. Though this Silicon Valley town is easily accessible from San Francisco, Palo Alto, San Jose and other Bay Area cities, the town has maintained a rural atmosphere and offers plenty of activities for day trippers.

Konditorei Cafe
Start your day off with some fresh coffee and bagels at Konditorei Cafe on Alpine Road. This local cafe has been serving Portola Valley and surrounding communities for over 30 years, and makes their bagels and pastries fresh each morning. When you’re finished with your coffee, stock up with a picnic lunch from the deli at Bianchini’s Market, located right next door.

Explore Windy Hill Open Space Preserve
This dog-friendly open space preserve offers miles of trails featuring sunny grassland ridges, shaded trails that wind beneath redwood, fir and oak trees, and expansive views from the top of Windy Hill. For a shorter hike, head to the Sausal Pond Loop. This 1.6-mile long loop is suitable for most users (kid-friendly), and will treat you to views of Sausal Pond, oak woodlands, and grassy meadows. To complete this loop, take Betsy Crowder Trail (hikers, equestrians) to its meeting point with Spring Ridge Trail (hikers, bikers, equestrians), and then take Spring Ridge Trail back down to the parking lot.

For the more adventurous hiker, take the Spring Ridge Trail all the way up to the iconic summit of Windy Hill. From this summit, enjoy 360-degree views of San Francisco, San Jose and the Pacific Ocean. If parking is full, check out other local open space preserves such as Pearson-Arastradero Preserve or Coal Mine Ridge Preserve.

Neely Winery
After your hike, relax with a wine tasting at Neely Winery, located right next door to the Windy Hill parking lot. Neely Winery’s newly opened tasting patio (March 2023) is located in a rustic barn with stunning views of the vineyards and nearby foothills. Their pinot noir, chardonnay, and grüner veltliner grapes are all grown and vinified on site, allowing you to experience a hyper-local taste of Portola Valley. These wines are from both the Santa Cruz Mountains AVA (American Viticultural Area) and the San Francisco Bay Area AVA. The tasting room is open Wednesday to Saturday from 11 a.m. to 5:30 p.m., tastings are by reservation only.

Alpine Inn
Finish your Portola Valley day trip with a meal at this historic beer garden, which has been a fixture of the area for over 170 years. It is the second oldest continually operating tavern in the state of California. Alpine Inn has an extensive menu full of traditional tavern specialties like burgers, fried chicken sandwiches and sausages, as well as options such as wood-fired pizzas, vegetarian smoked shiitake mushroom tacos, and bacon jam sliders. Be sure to try the banana pudding for dessert!

Special reminder from your Hilltromper family: Always remember to eat, drink, and recreate responsibly. We are all in this together!

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