From Harvest to Holidays: Insider Tips for Your Wine Country Escape
Fall is when wine country truly shines. The vines glow gold, mornings are crisp enough for a sweater and coffee on the patio, and the calendar fills with events that locals circle months in advance. As someone who calls this Sonoma County home, I’ll let you in on a little secret: the best way to experience these moments is with the right home to return to—and a concierge touches that transform a trip into something unforgettable.
Here’s how I’d spend the season, with Kohmsa homes that pair perfectly with each event.
Don’t Miss: The Sonoma County Harvest Fair
October 4–6, 2025 | Sonoma County Fairgrounds
If you want to feel the true heartbeat of wine country, the Harvest Fair is it. For 50 years, this event has been where locals and visitors gather to celebrate the season—think endless wine tastings, farm-to-table dishes, and yes, the famous grape stomp (messy, but worth it). My tip? Arrive early to snag a spot at the chef competitions, where Sonoma’s rising culinary stars put on quite a show.
Stay at Paradise Ridge Vineyard Estate
Perched above the vines with panoramic views, Paradise Ridge feels like you’re living inside a postcard. The fire pits and multiple hot tubs are perfect for cool October evenings, and with multiple homes on the property, it’s ideal for families and groups who want to stay connected without sacrificing privacy.
Kohmsa Touch: After a day of stomping and sipping, skip the lines at restaurants and return to a private harvest dinner, prepared in-home by a Kohmsa chef. Locally sourced ingredients, the wines you discovered that day, and a sunset view—this is Sonoma wine country living at its finest.
Local’s Shortlist:
Best Morning Stop: Avid Coffee Roasters in Santa Rosa for a a local favorite for smooth pours and a cozy start to the day.
Hidden Gem Winery Nearby: Benovia Winery—laid-back vibes, incredible wines, and a surrounded by acres and acres of vines.
Pro Move: Bring an extra pair of shoes for the grape stomp—you’ll thank me later.
Sip & Savor: Wine & Food Affair
November 1–2, 2025 | Sonoma Wine Road
This event is one of my personal favorites. Imagine more than 50 wineries opening their doors, each offering bites designed to complement their pours. It’s a choose-your-own-adventure of food and wine, and the joy is in discovering pairings you’d never expect. Pro tip: pace yourself and plan a midday stop at a smaller, family-run winery—you’ll often find the winemaker pouring behind the counter.
Stay at the Mid-Century Modern Marvel
This home was built for weekends like this. Sleek design, an outdoor kitchen for showing off your wine country finds, and a solar-heated private pool for lazy November afternoons. With space for four couples, it’s perfect for making the Wine & Food Affair a shared memory.
Kohmsa Touch: Leave the keys behind and let Kohmsa arrange seamless private transportation. Your driver will map out your tasting trail so all you need to do is sip, savor, and enjoy. When you return, we’ll have a curated wine-and-cheese spread in the gourmet kitchen.
Local’s Shortlist:
Best Pre-Tasting Fuel: Costeaux French Bakery in Healdsburg—legendary pastries and strong coffee.
Hidden Gem Winery: Matrix Winery—small-lot Pinot Noir, Zinfandel, and a laid-back setting tucked along Westside Road.
Pro Move: Grab a bottle or two of your favorites early—many sell out before the weekend ends.
Holiday Magic: Santa Train Jolly Journeys
November–December 2025 | Napa Valley
If you’re visiting with family, the Santa Train is a must. Kids love the storytelling and twinkling lights, and adults appreciate the gourmet bites and flowing wine—it’s a holiday tradition that truly delights all ages. Insider tip: book an evening departure for the most dazzling light displays along the tracks.
Stay at Trinity Oliveira Estate
This Glen Ellen gem feels like your own private holiday retreat. With vineyard views, designer interiors, and cozy spaces both indoors and out, it’s a home that encourages gathering—whether around the pool by day or a crackling fire by night.
Kohmsa Touch: To keep the holiday spirit alive, let Kohmsa transform your stay with in-home holiday decorating service. From twinkling lights to a tree trimmed with care, we’ll create a festive backdrop for your family celebrations.
Local’s Shortlist:
Best Family Brunch Spot: Model Bakery in St. Helena—their English muffins are worth the hype.
Hidden Gem Winery for Families: Ashes & Diamonds—with lawn games, retro design, and approachable wines, it’s a spot where adults can sip while kids stretch their legs.
Pro Move: Book the train early—weekend evening rides sell out fast.
The Kohmsa Stays Difference
Here in wine country, we believe in slowing down and savoring every moment. Kohmsa makes that possible. Beyond the homes, we’re your local guide and concierge in one—arranging private chefs, transportation, vineyard tours, wellness sessions, and seasonal touches that turn a trip into a story worth telling.
Ready to Plan Your Perfect Harvest-to-Holiday Escape?
Let our team curate your stay—from matching you with the perfect Kohmsa estate to arranging every thoughtful detail that makes wine country effortless.
Contact us today to begin your Kohmsa Stays journey.
