This Small California Town Has The Best Downtown
In the heart of Sonoma Wine Country, along the Russian River, sits a town known not only for its rolling vineyards but also for its energetic downtown district. That town is Healdsburg, California, home to roughly 11,300 residents. Of its over 80 wineries, an impressive 30 are located right near the central plaza. Over two dozen art galleries, meanwhile, are within walking distance of the downtown area. For the food lovers, there are even a couple of great Michelin-recommended restaurants to try! So lace up your walking shoes and join us for a stroll through the incredible streets of Healdsburg.
Wine Tasting on Healdsburg Avenue

If you want to enjoy a glass of wine without stressing about driving afterward, Healdsburg Avenue downtown is just the place. This street is packed with wineries and tasting rooms, many of which have their vineyards planted in the surrounding areas. You can begin your wine tasting adventure at Rockpile Vineyards, a tasting room near the intersection of Mill Street and Healdsburg Avenue that sources its wine exclusively from the Rockpile AVA. Tasting experiences here include four wine tastings, six wine tastings, and cheese and charcuterie boards for sale that complement the wines’ flavors.

Next, continue north on Healdsburg Avenue, stopping at Siduri Wine Bar and Tasting Lounge on the opposite side of the road. This tasting room is particularly cozy, boasting vinyl records and comfy seating, as well as wines from across California and Oregon. A couple of blocks up the road, you’ll hit Portalupi Wine. This Cal-Ital-style winery honors its Italian heritage through a refreshingly unique selection of wines, including Barbera and Arneis. You might forget that you’re in California by the end of the tasting!
Art Galleries & Museums

With numerous art galleries, you’ll be able to gallery-hop to your heart’s content downtown. The Paul Mahder Gallery is a beautiful place to start, located right on Healdsburg Avenue in a 1940s-era Quonset hut. This gallery is gorgeous, featuring over 8,500 square feet of gallery space and 30-foot-high ceilings, showcasing works from both national and international artists. The Bob Johnson Art Gallery is another fun stop to add to your itinerary, housed in the 1885 Gobbi building with an upstairs suite of galleries, a private art library, and a design studio.
Those interested in history should check out the Healdsburg Museum and Historical Society. This museum, situated in an old Carnegie library, is listed on the National Register of Historic Places. Inside, you’ll find an extensive permanent collection on local Native American groups, the town’s history since 1857, and an array of rotating exhibits.
Shopping & Dining

If you haven’t already noticed from your wine tasting and gallery hopping, much of Healdsburg’s commercial activity revolves around the Healdsburg Plaza. Here, and on the blocks surrounding it, you can find all kinds of restaurants and shops to explore. Quail & Condor is a favorite spot for breakfast, a neighborhood bakery and café that serves artisanal pastries, including croissants, scones, and biscuits. After breakfast, head over to some of the shops along the plaza, such as Forager: A Modern Mercantile. This local shop sells all sorts of gifts and home decor, including kitchenware, table top decor, glassware, vintage goods, and more.

You can catch the Healdsburg Farmers Market in the Healdsburg Plaza on Saturdays from April through December, plus on Tuesdays from May through September as well. Taking place since 1978, the market features items like produce, flowers, honey, olive oil, bread, cheese, and fresh eggs. For a memorable dinner, look no further than Barndiva, a Michelin-recommended restaurant that serves mouthwatering European-style dishes.
Hotels & Inns
There’s no better way to round out your trip downtown than by checking into one of the charming hotels or inns. Just a five-minute drive north of the Healdsburg Plaza, you can reach luxurious accommodations like The Lodge, a new boutique hotel in town. You’ll be able to enjoy all kinds of lovely amenities here, including an outdoor pool, a courtyard with fire pits, a sauna and steamroom, and a cafe and wine bar. Many of the rooms come with cozy touches as well, such as in-room fireplaces and soaking tubs.

If you’re hoping to stay a few blocks closer to the plaza, you’ll also love the Bella Luna Inn on Healdsburg Ave. Built in 1909, this local inn has been completely remodeled, providing guests with a luxurious night away. In addition to some wonderful amenities, this hotel provides guests with a gift card to have breakfast at a couple of nearby cafes and restaurants, allowing you to start the day on the right foot. Although closed for the season, this hotel will reopen on February 14th of the coming year. Right in time for a romantic Valentine's Day trip away!
A Walkable Downtown Filled With Adventure
If you are looking for a straightforward vacation this year, Healdsburg makes a great contender. You can leave your car parked for nearly the entire trip, focusing instead on exploring the walkable galleries, restaurants, museums, and wineries. Downtown hotels make your stay even better, with onsite wine bars, complimentary breakfasts, and cozy fire pits that add a little extra magic to your visit. The potential for adventure is practically endless!