Silicon Valley’s Hidden Gem: A Walkable Urban Wine Trail of Charming Family-Owned Wineries

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Silicon Valley's Hidden Gem: A Walkable Urban Wine Trail of Charming Family-Owned Wineries

South of San Francisco, nestled between San Mateo and Palo Alto (the “birthplace of Silicon Valley”), sits the tiny town of San Carlos. This industrial sliver of Silicon Valley is home to the little-known Mid-Peninsula Wine Trail, a walkable urban wine trail that includes a handful of family-owned, artisanal wineries.



Located just 25 minutes east of the laidback coastal city of Half Moon Bay by car, the tasting rooms on the wine trail in San Carlos are all located in the center of town, within a one-block radius of Industrial Road. The Industrial Arts District, as the area is known, has its fair share of fast food spots and dollar stores, yet the wineries, tasting rooms, restaurants, and local watering holes give the area a dose of unique urban charm.

Where to taste wine on the Mid-Peninsula Trail

When Anders and Vikki Vinther moved to California from Denmark, they never imagined they would become winemakers. Fast forward nearly 20 years and they are living their dream, sharing their wide range of Flying Suitcase Wines (including a Bordeaux-style collection) with visitors in their San Carlos tasting room. Meanwhile, Domenico is a boutique winery influenced by the family’s Italian heritage. Winemaker Dominick Chirichillo was inspired by his grandfather, who kept a wine press in the basement. While craftsmanship was passed down through generations, Domenico Winery represents a modernized version of handcrafted winemaking, complete with an osteria where it pairs traditional Italian dishes with its award-winning wines. 

Bob Mullen, the founder of Woodside Vineyards, has been producing wine in the area since 1960. The La Questa Cabernet Sauvignon is a historical gem as it’s made from grapes whose vines were originally planted in 1884. Sourced from the only acre remaining from the La Questa Vineyard, this exclusive cabernet is one of its specialties. Woodside wines can be tasted at the Wine Patio at Auto Vino on the weekends. Russian Ridge Winery is a second-generation father-son winemaking team who produce fewer than 1,000 cases of wine per year. At their tasting room, Scott and Spencer Townsend host tastings on the weekends and certain Thursday and Friday evenings. Finally, at Cuvée, what began as a passion project turned into a second career for owner Paul Rogerville. Now, the artisan winery puts out award-winning limited release, Bordeaux-inspired wines.

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If you’re feeling wined out, or if beer is more your thing, check out Devil’s Canyon Brewery. Also located in downtown San Carlos, it has been hosting Beer Fridays for over 20 years: Every Friday at 4 p.m., it opens to the public and welcomes guests (of all ages) to its sprawling property for craft beer, live music, and food trucks.



Plan your visit in and around San Carlos

Dave Pennells

By Dave Pennells

Dave Pennells, MS, has contributed his expertise as a career consultant and training specialist across various fields for over 15 years. At City University of Seattle, he offers personal career counseling and conducts workshops focused on practical job search techniques, resume creation, and interview skills. With a Master of Science in Counseling, Pennells specializes in career consulting, conducting career assessments, guiding career transitions, and providing outplacement services. Her professional experience spans multiple sectors, including banking, retail, airlines, non-profit organizations, and the aerospace industry. Additionally, since 2001, he has been actively involved with the Career Development Association of Australia.