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USA Travel: Healdsburg, California in Two Days, One Night – Activity Recommendations

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This is a list of activity recommendations for two days, one night in Healdsburg, California, USA, named one of the best small towns to visit in America. This itinerary includes visits to nearby wineries in Healdsburg.

If you are in San Francisco or coastal California, you may consider adding a couple of extra days to your plans so you can head inland to explore wine country.


About Healdsburg

  • The town is known for its organic farms, artisan food, talented artists, and premier wineries.
  • In 2014, Smithsonian Magazine named Healdsburg #2 in its list of “Best Small Towns To Visit.”
  • “The town centering Northern Sonoma County’s wine and tourism industry is as quaint as they come, with galleries, tasting rooms and all manner of gift shops lining a plaza so picturesque it feels like it could reside on Disneyland’s Main Street, U.S.A.” – Charlie Swanson,
  • Travel and Leisure Magazine named Healdsburg Plaza as one of the “most beautiful town squares in the U.S.”.
  • “The 20 Most Charming Towns and Cities in California” – Travelmag
  • “20 of the Top Places to Visit in the USA in 2019” – TripAdvisor

Map of Locations

Day 1: Arrive to Healdsburg

Arrive by private car to Healdsburg. Drop your bags off to the hotel and walk to the town square for a meal at any of the nearby restaurants, which may offer wine flights or tasting opportunities of local wine varietals.

Healdsburg is community-oriented and hosts arts, music and cultural events throughout the year. Ask around or check local listings to see what’s on while in town. We stumbled upon a jazz festival and farmer’s market on the same day.

Healdsburg’s Town Event’s Calendar:

Join in one one of the city’s “Tastemaker Tours” that aim to highlight the attributes of the region. Savor Healdsburg Food Tours and Wine Country Walking Tours have crafted one-of-a-kind, thoughtfully planned adventures inspiring participants to go beyond the typical wine country experience and partake in intimate interactions with local artisans, chefs, and masters.

In the late afternoon, take a Lyft/Uber to Matrix Winery for a tasting.

Maxtrix Winery offers panoramic views of the Russian River Valley. Selecting a tasting flight from their critically acclaimed wines, that include Pinot Noirs, Zinfandels, Petite Sirah, Cabernet Sauvignons, Chardonnays and Bordeaux varietal blends.

Vistor information:

Map from downtown Healdsburg to Matrix Winery

Stay at the Grape Leaf Inn, a charming, boutique Victorian Inn, just blocks from the Healdsburg Plaza and its many shops, restaurants and tasting rooms.

Grape Leaf Inn:

Day 2: Wine Tasting in Healdsburg — Comstock Winery & Wilson Winery

Enjoy a mid-morning breakfast prior to departing for an early wine tasting at Comstock Winery. Many wineries open at 11 AM – check their schedule before departing. The property is expansive – ask if tours are available.

“Comstock Winery began in 2002 by owners Bob and Sandy Comstock. They began growing grapes in Sonoma County’s Dry Creek Valley and the idea of creating a boutique winery was born. In 2012, the 17-acre vineyard in Dry Creek Valley became available and the idea of a winery became a reality. The winery opened its doors in August 2015, featuring Zinfandel, Cabernet Sauvignon, Pinot Noir, Merlot, Sauvignon Blanc, Viognier and Chardonnay.”

Visitor information:

Map from downtown Healdsburg to Comstock Winery

Continue down the road to Wilson Winery. This winery is known for its Zinfandels crafted in the heart of Dry Creek Valley.

Visitor information:

Map from Comstock Winery to Wilson Winery

Return to downtown for a late lunch.

Depart south to San Francisco (a 1 hour, 30 minute drive) or continue your tour of wine country.

Connect this itinerary:

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