Growing up in the Bay Area, I had the immense fortune of spending time in California’s wine country long before I knew just how special it truly was. With an uncle in Petaluma and a father who retired to the Healdsburg area, the Russian River Valley became a regular escape for our family. And while it’s stunning year-round, there’s something about autumn—especially October—that makes it my absolute favorite time to visit.

Picture this: crisp air, golden vines, fewer crowds, and that magical late-afternoon light that seems tailor-made for a glass of Pinot Noir. Fall in wine country is the perfect blend of sensory indulgence and seasonal serenity.

Let’s start where the magic happens—the wineries. I always make time for MacRostie, perched on a hilltop with sweeping views of the Russian River Valley. Their single-vineyard Chardonnays and Pinot Noirs are matched only by the warm hospitality and sleek, modern tasting room. In the heart of Healdsburg, Marine Layer is a must-stop for its cool, coastal-inspired wines and chic design aesthetic. Flowers—with its elegant wines and stunning architecture—offers an immersive experience that’s both stylish and soulful.

For something a bit more off-the-beaten path, DaVero Farms & Winery brings a biodynamic, Italian-inspired approach to wine and olive oil. It’s like sipping in Tuscany, but with a Sonoma zip code. Then there’s TWOMEY, a sibling winery of Silver Oak, where the Pinots are plush, and the porch is perfect. Finally, Aperture Cellars—a modern marvel founded by a photographer and winemaker—feels more like an art gallery than a traditional winery, making it a feast for both palate and eye.

To stay in style, Montage Healdsburg is the crown jewel. Nestled among 250 acres of rolling vineyards and oak trees, this luxury resort offers a wine country experience that’s as elevated as the hilltops. Think treehouse-style suites, a world-class spa, and a wine list that rivals the tasting rooms themselves. It’s worth the splurge.

Now let’s talk food—because what’s wine without a little culinary indulgence? SingleThread, a three-Michelin-star sensation, offers an unforgettable farm-to-table tasting experience that showcases the best of Sonoma. Barndiva combines rustic elegance with seasonal, locally sourced ingredients, while Valette is a favorite among locals and visitors alike for its approachable fine dining. For something more casual, 

The Matheson brings rooftop vibes and killer pizzas, and Dry Creek General Store offers the kind of hearty sandwiches you dream about mid-tasting flight.

Getting around is easier than you’d think. If you're flying in, Sonoma County Airport is the closest (and most charming) option, although there are more flights in and out of San Francisco and Oakland. From there, you can rent a car or go all-in on a private driver—my recommendation if you plan to sip generously. Several companies, like Pure Luxury Transportation, offer half and full-day tours that handle both navigation and narration.

Want to do more than just sip? Take a bike tour through the vineyards with Wine Country Bikes, or paddle down the Russian River for a little nature with your Nebbiolo. If relaxation is the goal, the Montage Spa offers vinotherapy treatments (yes, wine facials are a thing) or book a yoga session overlooking the vines.

Whether it’s a romantic getaway, a girls’ weekend, or a solo recharge, fall in the Russian River Valley and Healdsburg is magic. It’s a place where wine flows, the leaves glow, and time slows. And for this Hilltop local who still considers the Bay Area home, it remains one of the most special corners of California to sip, savor, and stay awhile.