Sandwiched Between Silicon Valley And Santa Cruz Is California's Unsung Wine Town With Victorian Charm

Nestled in the inland foothills of the Santa Cruz Mountains, 22 miles from Santa Cruz and 14 miles from Silicon Valley, Los Gatos is a charming town known for its upscale, pedestrian-friendly downtown, beautifully preserved Victorian architecture, and effortless air of affluence. It's the kind of place where dining out is a slow, social affair, and boutique window displays are works of art. 

Settled in the 1840s, Los Gatos grew in parallel to Francisco's Gold Rush boom, depending instead on logging, milling, farming, and canning. A stroll through Los Gatos' pristine residential neighborhoods reveals hundreds of Victorian-era homes, including ornate English Queen Anne-style houses that look straight out of Architectural Digest. Despite the manicured streets, Los Gatos has always maintained an intimate connection to the surrounding forests. In fact, the town originally bore the name "La Rinconada de Los Gatos" — Cat's Corner in Spanish — due to the yowling cries of mountain lions prowling through the hills. 

Nowadays, mountain lions mind their own business, but Los Gatos still serves as a jumping-off point for exploring the Santa Cruz Mountains' hiking and biking trails, including routes winding through ancient redwood groves. For impressive redwood views all the way to the ocean and a hidden waterfall, visit Castle Rock State Park and hike the 4.8-mile Saratoga Gap and Ridge Trail Loop. Alternatively, Big Basin Redwoods State Park, California's oldest state park, boasting giant, ancient trees, incredible trails, and backcountry beauty, is only 18 miles away.           

Bay Area locals know Los Gatos as the best place to wait out traffic going over Highway 17 or plan a romantic date night, but visitors can also take advantage of the Michelin-caliber restaurants and underrated wine scene. At The Bywater, a New Orleans-style restaurant serving Cajun and Creole fare prepared with farm-fresh, seasonal ingredients, the daily happy hour is a local legend. The restaurant earned a coveted Wine Spectator Award of Excellence three years in a row, so wine aficionados will be happy, and the crispy fried oyster po' boy is simply unbeatable.

Los Gatos is also home to numerous tasting rooms with an emphasis on single-vineyard Chardonnays and Pinot Noirs, ranging from chic downtown nooks to refined estates reminiscent of the Tuscan countryside. Sit beneath vine-covered arbors and shady olive trees at Regale Winery and Vineyards, or sample bold vintages in a classic stone cellar once part of a 19th-century Jesuit-run wine operation at Testarossa Winery. Visit Gali Vineyards' family-run tasting room in downtown Los Gatos to try the Tempranillo flight (call in advance to make sure it's available) — tasting the differences between the vintages is a real treat. 

Complete your tour of the South Bay's vineyards with a stop along Santa Cruz's dreamiest wine trail that features rolling hills, celebrated wines, and sun-drenched patios, or continue south to Carmel Valley and avoid the crowds of Napa at this picturesque, under-the-radar wine destination.

Although Los Gatos may have a population of only 32,000 people, there's still tons to do. Visit the Montalvo Arts Center for an array of cultural and art experiences surrounded by hiking trails through the rolling Saratoga Hills. Built in the Mediterranean Revivalist style, Villa Montalvo is a masterpiece in its own right, and the knowledgeable volunteers will tell you all about its history. Guided tours are only available by appointment and also include an optional hiking add-on. 

After exploring Mantalvo Arts Center's extensive grounds, discover community-driven art and history exhibits at New Museum Los Gatos. Past exhibits have included "Snapshots of Pride: Photographer Ted Sahl's Chronicle of the South Bay LGBTQ+ Community" and numerous shows highlighting the cutting-edge work of local creatives. While exploring downtown Los Gatos' independent boutiques and high-end fashion shops, stop by Whitney Modern, a must-visit gallery for contemporary fine art collectors and enthusiasts in Silicon Valley.

Los Gatos is beautiful year-round, but one of the best times to visit is in September during the Los Gatos Art and Wine Festival. For over 50 years, the festival has featured around 200 local artists, live music, and wine from across the region. Plus, the food trucks will ensure you're never hungry for even a moment. Admission is free, but you'll have a hard time leaving without splurging on a few treats.