The Cheapskate’s Guide to Healdsburg

The Cheapskate’s Guide to Healdsburg

Healdsburg offers a well-considered mix of high-brow and low-brow, sophisticated and simple
By Virginie Boone
Courtesy Little Saint

August 14, 2023

The Sonoma County city of Healdsburg may feel like a tony town full of luxurious experiences, and it is, in many ways. But it wasn’t all that long ago that Healdsburg was better known as the “Buckle of the Prune Belt,” with plums planted on thousands of acres and horses parked around the dusty central plaza. 

That early tie to agriculture remains. One hour north of San Francisco, Healdsburg is surrounded by several of the best-known appellations for wine grapes in the world, including the Russian River, Alexander and Dry Creek valleys, and Chalk Hill.

With fine wine has come fancy food and resorts and tasting rooms, but while Healdsburg has elements of movie-set charm, it retains much of its more rugged, rural character, too. 

Today, the town is a well-considered mix of high-brow and low-brow, sophisticated and simple. You certainly don’t need to spend big to enjoy the pleasures of Healdsburg, so here are a few suggestions for enjoying one of the world’s great wine towns, no crazy budget required.

Little Saint Healdsburg


  • Little Saint is a restaurant, café and all-day lounge with a relaxed vibe. It also boasts a 500-bottle wine shop that will pour you wine by the glass from its retail selections. 
  • Lo & Behold is a beloved locals’ comfort food and drink place run by locals with “Snacks, Smalls & Shares” that taste great at any price. 
  • Happy hour at Spoonbar means $10 cocktails and $10 truffle fries on a nightly basis. Go get them. 
  • For the more adventurous, venture down to the Dry Creek General Store’s historic wooden bar, first opened in 1881. It doesn’t seat a lot of people or get too fancy on the drinks, which is exactly how the regulars like it. 
  • For something non-alcoholic, especially on a hot day, head to Amy’s Wicked Slush—it sits right on the Russian River— for imaginative slushes, slushballs and soft-serves. 


  • Hometown chef Dustin Valette’s The Matheson is a knockout fine dining spot, but locals go up a few floors from the main restaurant to open-air Roof 106 for small, shareable plates and cocktails. The views and fire pits make it a comfortable place to lounge and socialize day or night. Quality hot dogs and sausages aren’t the first thing that come to mind in a fanciful wine region, but boy are they welcome. 
  • The Wurst makes a range of homemade sauces to go with its brats, Polishes, Italians and more. There’s even a Not Dog veggie sausage made from chickpeas. 
  • You can’t be in this part of California without running into really well-made Mexican food. El Farolito is a longstanding family-run standout that makes a killer mole negro. 
  • In the mornings, get your baked goods at Downtown Bakery & Creamery, a local institution. The sticky buns are famous. 
  • Troubadour has all you could ever want in a French-style boulangerie. But mostly you’re here for the grab-and-go ham and butter baguette sandwiches.


  • Ciao Bruto! Wine & Provisions specializes in organic grower-producer wines from Italy and France, as well as the to-be-expected tinned fish, sardines and conservas. Hit this spot to round out your picnic basket. 
  • Maison Wine Bar carries some of the finest wines in the world, so it’s not necessarily a place to be cheap, but it is a good place to try many of these hard-to-seek wines and sakes by the glass, rather than having to spring for a full bottle.

Taste (Wine)

  • Matt and Alexis Iaconis cut their teeth working for four-star Michelin restaurants, but their wine brand Brick and Mortar features a nice range of still and sparkling wines that are light in style and budget. Tastings by appointment are casually held in their barrel room. 
  • Idlewild is Sam Bilbro’s minimalist interpretation of Piedmont in California; the wines are vibrant, delicious and very fairly priced. 
  • At Cartograph, you can taste six wines for $30, including two regional Rieslings and Brut Zero sparkling wine. 
  • If you travel farther afield into the Russian River Valley, you can taste at one of the most historic names in Pinot Noir, Rochioli Vineyards and Winery. Overlooking its much sought-after vines, the tasting room has a $25 estate flight of four killer wines that’s a steal.


  • Created by the construction of a dam in 1983, Lake Sonoma, when full, covers 2,700 acres, with 50 miles of coastline. It’s a local hub of boating, hiking, camping and other outdoor activities. Lake Sonoma is easy to get to from Healdsburg, and a pretty drive through the Dry Creek Valley appellation. Sitting high above the lake is the Rockpile appellation, with its rich rocky soils. Once you’re there, the marina is equipped with deli goods, beer/wine and boat rentals. A five-person pontoon boat can be rented for either half a day ($250) or full day ($550) excursions. Or get a kayak, paddle board or canoe for $35-$40 an hour. 
  • The Ranch at Lake Sonoma offers horseback riding. A lot of the trail rides ($69-$129/person) overlook beautiful vineyard land. You can add a boxed lunch for just $25.
  • There aren’t a lot of live music venues in this wine town, but among the most understated—and most fun—is Elephant in the Room, a pub run by locals, for locals. This music joint offers hand pies, hot dogs, local brews and a regular roster of live music by bands with names like Electric Tumbleweed and Boot Juice. Don’t overthink it.


  • Even the thrifty need a reason to let loose and spend every now and again. So here’s a good one: Michelin-starred Barndiva has been a favorite since it opened nearly 20 years ago with the mantra “Eat the View.” The restaurant celebrates everything there is to love about Sonoma County’s agricultural scene and well-earned reputation for fine food and drink. The menu samples from the gardens and ranches of locals (including its own) for many of its ingredients, while the wine and cocktail list offers all the standards, but still has the ability to surprise. If you’re in town for one of the restaurant’s great special events—including its popular springtime Pink Party, summer Fête du Vin Blanc or harvest-themed Fête Rouge in the fall—spring for a spot. You won’t regret it. (Also of note: Barndiva’s world-renowned bartender/forager Scott Beattie offers cocktail classes).