These Favorite Windsor and Healdsburg Restaurants Are Worth Rediscovering

Discover some of Sonoma County's charming neighborhood restaurants, where servers know your name, prices are reasonable and the drinks are stiff.


Neighborhood restaurants are the lifeblood of Sonoma County’s food scene, where servers know your name and order as soon as you walk in. Prices are usually reasonable, kids welcome, drinks stiff and there are plenty of opportunities to run into old friends. Some have been around for decades while others just seem to fit in right when they open.

Recently, I’ve been visiting some favorite old haunts worth discovering (or rediscovering).

Pizzando

Healdsburg in the daytime can be slow as a sloth. But come dusk, restaurant lights flood the streets and the party heads outside to semi-enclosed sidewalk parklets. Strolling past Pizzando, it’s hard not to notice al fresco diners — families, couples, friends — huddled around Neapolitan pizzas and hulking plates of pasta. It’s a delicious advertisement for the 12-year-old restaurant after a significant menu overhaul and interior expansion in 2023, something sorely needed at the longtime Hotel Healdsburg trattoria.

Pizzando restaurant in Healdsburg
From left, Lori Taylor, Phyllis Sutton and Tracy Garrison grab a pizza for lunch from Pizzando on a day out in Healdsburg, Friday, June 2, 2023. Pizzando now offers an extended menu with hearty entrées, as well as a full bar. (John Burgess / The Press Democrat)

Launched with just a handful of tables, a woodfired oven and little else, the restaurant was an also-ran in the glitzy, over-the-top Healdsburg restaurant scene for years.

That’s changed.

Pizzando now offers an extended menu with hearty entrées (lasagna and osso buco are favorites), excellent pasta, burgers and antipasti, a well-thought-out wine list (both local and Italian) and a full bar.

It’s also one of the few all-day restaurants downtown, offering their full menu from 11:30 a.m. to 9 p.m. and a weekday happy hour from 3 to 5 p.m.

Pizzando
Cocktails from Pizzando in downtown Healdsburg. Pizzando has a well-thought-out wine list and full bar as well as a weekday happy hour from 3 to 5 p.m. (Courtesy of Pizzando)
Best Bets

Preserved Lemon Ravioli ($25): stuffed with creamy ricotta, the extra-large ravioli swim in a lemon-butter sauce you’ll be licking from the bowl (we used our extra pizza crust).

Melanzane alla parmigiana ($21): You’ll be eating on this for days, which is just fine, considering the mix of tart tomato sauce, baked (not fried) thinly sliced eggplant and globs of melty, stringy mozzarella happily melding into a tummy-filling treat.

Elderflower Spritz ($14): Aperol is out, and sassy St. Germaine elderflower liqueur is in. More delicate and less bitter, this fizzy spritz is a refreshing foil for all the cheese and carbs you’ll consume.

301 Healdsburg Ave., Healdsburg, 707-922-5233, pizzandohealdsburg.com

El Milagro Healdsburg

A charming, tucked-away cucina offering authentic regional Mexican cuisine from the owners of El Milagro in Cloverdale. While Healdsburg isn’t lacking in Mexican restaurants — from higher-end cafés to everyday taquerias — I’ve long been a fan of the bighearted, family-inspired dishes from chef-owners Alan Valverde, Julio Velazquez and Marco Zamora.

Open from 11 a.m. to 9 p.m. daily.

From El Milagro restaurant in Healdsburg
Mole Verde Pipian, braised chicken breast in housemade green pumpkin seed mole sauce from El Milagro Healdsburg, Friday, Nov. 1, 2024, in downtown Healdsburg. (John Burgess / The Press Democrat)
Traditional pre-Hispanic Mole Rojo with a mix of spices perfected by co-owner Julio Velazquez’s mom from El Milagro Healdsburg, a block west of the square Friday, Nov. 1, 2024, in downtown Healdsburg. (John Burgess / The Press Democrat)
Traditional pre-Hispanic Mole Rojo with a mix of spices perfected by co-owner Julio Velazquez’s mom from El Milagro Healdsburg, a block west of the square Friday, Nov. 1, 2024, in downtown Healdsburg. (John Burgess / The Press Democrat)
Best Bet

You’re here for the mole, specifically, the Mole Verde Pipian (green pumpkin seed mole, $22) made with chiles, spices and crushed pumpkin seeds with braised chicken.

Even better is pork Mole Rojo ($22), an ancient recipe that predates the Spanish and is “a melody of the owners’ moms’ recipes.” Long stewed pork is infused with the sweet, bitter, intensely flavored sauce made with over a dozen ingredients. My new favorite mole.

14 Matheson St., Healdsburg, 707-385-4672, milagrohealdsburg.com

Kin

Kin restaurant in Windsor
Kin restaurant in Windsor Monday, Nov. 17, 2014. (Crista Jeremiason / The Press Democrat)

After 13 years in business on the Windsor Town Green, it’s easy to take this neighborhood restaurant for granted. However, the fact that I end up here so often with friends and family speaks to its broad appeal and well-made comfort food ranging from burgers and frickles to braised short ribs, mac and cheese and warm cobbler.

Hospitality industry veterans Brad Barmore and JC Adams intentionally created a casual restaurant with something on the menu for everyone without feeling like a compromise.

Open from 11 a.m. to 9 p.m. Sunday to Thursday, until 10 p.m. Friday and Saturday.

from Kin restaurant in Windsor
Mac and cheese at Kin restaurant in Windsor. (Heather Irwin/The Press Democrat)
Best Bets

Braised Short Rib ($30): Red wine-braised beef short rib piled on cheesy polenta is cozier than a cashmere sweater.

Kin Mac & Cheese ($18): An entree-sized, shareable portion of cavatappi pasta bathed in white cheddar bechamel sauce, topped with Parmesan bread crumbs. Carbs + cheese + bread crumbs = pure happiness.

740 McClelland Drive, Windsor, 707-837-7546, kinwindsor.com

You can reach Dining Editor Heather Irwin at heather.irwin@pressdemocrat.com. Follow Heather on Instagram @biteclubeats.