6 Fun Things to Do in Healdsburg

Healdsburg Plaza

Beautiful, historic, and surrounded by rising hills and vineyards, Healdsburg is a picture-perfect Sonoma Wine Country town.

Nestled against the Russian River in northern Sonoma County, Healdsburg holds the charms of a small, agricultural community with the amenities of a world-class wine and food destination. With its hip boutique hotels and gracious B&Bs, it’s a convenient take-off point for wine-tasting and cycling adventures and just a short hop from the Russian River Valley. However, don’t be surprised if Healdsburg’s seductive charm causes you to slow down and enjoy the town.

1. Explore Healdsburg’s Historic Plaza

Storefronts along Center Street in downtown Healdsburg, Sonoma County
Center Street in downtown Healdsburg

One of the best, easiest, and most fun ways to get familiar with Healdsburg — named one of the nation’s six “Most Romantic Small Towns” by CNN Travel — is to take a leisurely stroll in and around its 19th-century plaza. At the center is an old-time band shell that’s still used for concerts and community gatherings. A small fountain entertains children while large redwood trees stand on the corners, watching over friends meeting for coffee and visitors enjoying the sun.

Shop boutiques, browse bookstores and art galleries, or relax in a coffee shop. If you feel like it, walk beyond the plaza to delight in beautiful 19th and early 20th-century homes. As you meander, check out the menus posted in the windows of heralded restaurants (more on that below!).

2. Sip Your Way Through Healdsburg Wineries

Three premier wine valleys — the Alexander, Dry Creek, and Russian River — meet near Healdsburg, and other noted wine regions, like Chalk Hill and Knights Valley, are nearby.

A great way to explore the many wineries of Healdsburg is to visit the tasting rooms that dot the plaza, including Thumbprint Cellars, Furthermore Wines, Hartford Family WineryWilliamson Wines, and more. Specializing in cool-climate Chardonnay and Pinot Noir from the Sonoma Coast, Marine Layer Wines is a boutique winery with a fireside lounge, comfy couches, and bright, inviting interiors courtesy of Sonoma designers HommeBoys.

For a uniquely Sonoma County experience, pair your wine tasting with a round of bocce ball. This game, which dates back to the Roman Empire, has long been popular in these parts thanks to the many Italian immigrants who settled in Sonoma County in the 19th century. Kick back with a glass of red at these Healdsburg wineries with bocce courts:

  • Armida Winery, housed in a geodesic dome, has killer views, three beautiful picnic areas, and a full-size bocce ball court.
  • Davis Family Vineyards, steps from the Russian River, invites you to stroll through its organic garden and join in on the bocce court. 
  • De La Montanya Winery offers a picnic area and bocce ball court shaded by a lovely apple grove (both are reserved on weekends for wine club members).
  • Dry Creek Vineyard has a bocce ball court next to one of its famed vineyards.
  • Seghesio Family Vineyards, one of the county’s pioneer wineries, offers a beautiful picnic grove where you can play bocce in the shade of oak trees.
  • Thomas George Estates lets you reserve the bocce court on its beautiful estate for fgroups of four to 12 players.  

Another way to get a taste of Healdsburg is a multi-day pass from Wine Road. These passes include special offers from wineries in the area, including complimentary wine tasting and discounts on wine purchases.

Other outstanding Healdsburg wineries include Wilson Winery, Rodney Strong, Ferrari-Carano, Pezzi KingMill Creek, Foppiano, and many others.

Check our listings of all Sonoma County Wineries and click on Healdsburg.

3. Sample Farm-to-Table Cuisine at Healdsburg Restaurants

Exterior of Valette, a popular Healdsburg restaurant, at night.

Healdsburg claims one of the most vibrant and buzzworthy dining scenes in Sonoma County — and all of Northern California, for that matter. That largely started with Kyle and Katina Connaughton, whose exquisite SingleThread Farm Restaurant and Inn has been honored with Three Michelin Stars and a rare Michelin Green Star.

Barndiva rated One Michelin Star, has been a Healdsburg favorite for two decades. The upscale country cuisine is sourced almost entirely from local farms and food producers. Grab a seat on the outdoor patio, crisscrossed with sparkling string lights, for a magical meal under the stars.

Another Healdsburg restaurateur, Dustin Valette, runs two must-visit eateries showcasing local and seasonal fare: Valette and The Matheson. Costeaux French Bakery is a favorite for pastries and delicious breakfasts.

4. Meander Through an Extraordinary Garden

The gardens in bloom at Ferrari-Carano Vineyards and Winery, Healdsburg
Ferrari-Carano Vineyards and Winery

With five acres of dazzling gardenscapes, Ferrari-Carano Vineyards & Winery on Dry Creek Road is a study in color nearly year-round. The gardens are Italian/French in style, with classic, geometric shapes forming an architectural backbone.

The color scheme and plantings change constantly throughout the year but always begin with a vibrant display of more than 10,000 tulips and daffodils each spring. Explore at your own pace on a self-guided tour, meandering along pretty paths, passing waterfalls, and crossing footbridges arching over gentle streams. More than 2,000 species of trees and shrubs sport identification tags, so you’ll learn while you wander.

To ascertain when tulips will bloom in spring, phone the Gardens’ Tulip Hotline at 707-433-5349, beginning in late winter. 

5. Enjoy a “Sip &  Cycle” Adventure

A woman cycles past rows of green vineyards
Highway 128, Alexander Valley

Where else but Wine Country can you get a good workout between sampling top-tier wines? Here, you’ll find one of the world’s best wine-cycling routes, a 30-mile loop that starts and ends in Healdsburg and takes you through the Dry Creek and Alexander Valleys. Whenever you feel like it, pull off to a winery to relax over a glass of wine, and then continue on.

Another great but shorter route: Alexander Valley’s Red Winery Road, between Healdsburg and Geyserville. It’s flat, quiet, and peaceful, running through beautiful oak-covered hills and miles of vineyards. For directions for either route, read “Popular Bike Routes Through Sonoma Wine Country.”

6. Explore the Healdsburg Museum

Housed in a former Carnegie Library, the Healdsburg Museum & Historical Society, built in 1910-1911, is listed on the National Register of Historic Places. The museum’s focus — the history of Healdsburg and surrounding areas — may seem geared to locals, but the creative exhibits showcase universally appealing points of interest. Permanent exhibits look at local Pomo and Wappo Indian tribes, Healdsburg’s early architecture, and much more. 

For more fun things to do and see, discover: 48 Hours in Healdsburg, Guide to Restaurants in Healdsburg, and Healdsburg Area Hotels with Vineyard Views.


Written by Sonoma Insider Suzie Rodgriguez

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