A Weekend in Healdsburg


Healdsburg is one of our favorite places to visit. Since Alex and I are members at Reeve, we visit at least quarterly to go pick up our wines. Since Healdsburg is only about an hour and a half north of San Francisco, we usually do it as just a day trip. But this time, we decided to make it a weekend by staying from Friday to Sunday in the town of Healdsburg when I had a wedding in the area.

Healdsburg has become quite the foodie destination, and it seems like every time we go, there’s some long-anticipated thing that’s newly opened. This time we got to visit Little Saint, the new vegan outpost by the SingleThread team; the newly redone Madrona Inn; and Flowers Winery.

Our cute little cottage had the best front porch and was just steps from the town square.

Little Saint is the new concept by Kyle and Katina of SingleThread. It’s part marketplace, selling fresh flowers and produce and other boutique food items; part cafe; and part restaurant. 

Chef Kyle Connaughton stopped by the kitchen!

Everything in the building is a wonderful farm-forward celebration of vegetables! Delicious, of course. With really tasty drinks as well.

Afterwards, ice cream from Noble Folk.

Porch life!

This was our first time visiting the Healdsburg Farmer’s Market. Nice to be so much closer to where the farms are actually located!

Quick sandwich from Oakville Grocers, eaten back on our front porch before I went off to work.

Day two began with breakfast at The Parish Cafe, which nicely mimics a New Orleans aesthetic.

Quail and Condor, the beloved local bakery.

Another jaunt around the town square.

Still working on knitting my little hexagon puffs for a quilt, wherever I go.

Then we had lunch at the newly redone Madrona. Boldly decorated by Jay Jeffers, with food from Michelin-starred chef Jesse Mallgren.

So good! The okonomiyaki was our favorite.

Such a fun vibe, with so many details to take in all over the property.

We followed up the lunch by wandering around the grounds, and then we had drinks on the front porch.

Last but not least, we visited Flowers Winery for a lovely outdoor wine tasting, paired with small bites.

The site was recently renovated and rebuilt in 2020, and the building has  since been lauded for its architecture. I like the clean lines and the use of wood all around. 

Each group got a little cabana outside for the tastings.

Another lovely trip through Healdsburg! I’m sure we’ll be back again soon.

Anna Wu is a wedding and portrait photographer based in San Francisco. She compulsively documents and blogs all of her daily adventures, even in quarantine. Follow her on instagram and view more of her professional work at annawu.com.