Head to Healdsburg, Wine Weirdos

Healdsburg is weird. Not like an uncle. It’s weird-good. Weird as in too good to be true.

Some places wear this kind of charm a little too proudly for my taste. Where every storefront feels “optimized.” Every interaction feels commercially rehearsed. Every restaurant feels like an Instagram post.

Healdsburg isn’t one of those places.

My buddy, who lives just ten minutes north, summed it up on a recent trip my wife and I took. He told me, “Napa is, ‘Do you have a reservation?’ And Sonoma is, ‘Welcome in.'”

People in and around Healdsburg don’t seem interested in performing hospitality. They just happen to be hospitable. You’ll end up chatting with the person pouring your wine. The concierge will happily spend fifteen minutes talking through hiking trails, favorite restaurants, or where to catch live music that night. Walk into just about any shop, and you’ll leave knowing a little bit about the person behind the counter.

And it’s not just that everyone is friendly. Everyone also seems to have their own thing going on. A winemaker who also paints. A chef who used to be the drummer of a band you’ve definitely heard of. A vintage dealer who has a hilarious story about working with Joan Rivers once. Nobody seems to be trying very hard to be interesting. They just are.

Healdsburg wasn’t trying to impress me. And that’s why it did.

Everyone walks around with an openness, an honesty, a curiosity, as if they’ve had two glasses of wine with lunch. Truth be told, they probably have.

Fly into SFO, rent a car, and point it north. Little by little, the scenery changes. Glass office buildings give way to rolling vineyards. Waymos hauling tech bros become dusty pickup trucks hauling grapes. The pace softens. So do you.

The drive to Healdsburg takes about 90 minutes, but it took my wife and me a little over two hours. Because we stopped at Grossman’s Noshery in Santa Rosa for lunch. It’s exactly the kind of place you’ll wish existed back home. Think classic neighborhood deli, except the wine list is as good as the sandwiches. It’s the kind of stop that turns your “drive” into your “opening act.”

We checked into Hotel Healdsburg, and it wasn’t, “Here’s your key, there’s the elevators, next guest please!” It was, “How was the ride in? What brings you to town? Here, have some free wine from a nearby vineyard.” I had to adjust my settings. I was coming off of a busy work gig in San Francisco, and it took me a minute to ease into this pace. I appreciate when life nudges me to slow down. This whole trip would become a giant nudge.

We listened to live jazz in the lobby bar one evening. Took our coffee by the pool one morning. Enjoyed the robes and slippers after evening showers. Hotel Healdsburg had free bikes for guests to use. We didn’t get around to the spa this trip, but that looked nice, too.

Most mornings, I’d bring my laptop down to the lobby to get a little work done over breakfast. Before long, I’d find myself eavesdropping on conversations between guests and the concierge, who always seemed to have another recommendation ready. A hidden tasting room. A scenic bike ride. A hike through the redwoods. A restaurant I’d never heard of. It felt less like talking to hotel staff and more like asking a well-traveled friend what we should do next.

Other places we considered:

• Montage Healdsburg
• Luxurious Wine Country Estate in Geyserville
• Liora Estate

There are people who like talking about wine. And there are people who like drinking it. I’m firmly in the second camp. And I recognize the irony of writing an entire section about wine after saying that. But here we go.

I insist you visit Martha Stoumen’s tasting room. Preferably early in your stay. For two reasons.

One. Her tasting room experience embodies everything my wife and I loved about Healdsburg and Sonoma. The atmosphere is elegant but not stuffy. It’s really interesting wine but not in a way that feels like homework. Andy led our tasting, and within sixty seconds it felt less like a presentation and more like a conversation, less like a tasting and more like talking to a farmer about food. Or a guitar player about their favorite band. Genuine passion. Genuine expertise. Shared in a way that made me more curious about what was in my glass instead of self-conscious about what I was supposed to taste. Some wine tastings are listening to a tour guide recite a script. Martha Stoumen’s is like spending time with a person who grows grapes.

Two. The reason you want to start here is so you can buy a case and have great wine for the rest of your trip. The prices are right, too, and you can join their wine club online. The 12-bottle club starts at just $480, and yes, they ship.

Other wine spots we enjoyed:

• Roof106 at The Matheson, Healdsburg
• Little Saint, Healdsburg
• The Punchdown, Sebastopol (Also have a location in Oakland)
• Dry Creek General Store, Healdsburg

Give me good wine, good company, and sunshine, and I won’t complain about wanting more. But Sonoma just so happens to have more. Who am I to argue?

One day, we traded vineyards for towering redwoods at Armstrong Redwoods State Natural Reserve. Place looks like a fairytale. Honestly, about halfway through our stroll, I was kind of expecting an elf to pop out from behind one of the giant trunks. Walking beneath trees that have been standing for more than a thousand years has a way of shrinking whatever felt important that morning.

From there, we headed for the coast. About an hour on the road and wine country gave way to crashing waves, rocky cliffs, and fishing towns that feel like they’ve been ignoring trends for decades. Happily. We ate at Rocker Oysterfeller’s in Bodega Bay. Took in the sunset from a lookout nearby. Our local friends told us about how they like to grab tacos from Fishatarian and head to Portuguese Beach for a picnic.

Another morning, we wandered out to the Sonoma Lake Overlook trail. Took in the views. Stopped at Dry Creek General Store for lunch on the way back.

One evening, we drove up to Cloverdale to watch one of our friends perform in Leading Ladies at the Cloverdale Performing Arts Center. Maybe I’m biased, because seeing people you love do what they love is love, but the production was fantastic. Check the theater’s schedule while you’re in town.

The Antique Society in Sebastopol is an absolute treasure hunt. Shop until you drop… into The Punchdown (nearby) for a bottle after.

And the little main square of Healdsburg is lined with boutiques and art galleries. Spend an afternoon walking around without a plan.

There’s probably a scientific explanation for the relationship between great wine and great food. But in Sonoma, it felt more like art to me.

One evening, we grabbed a table on the rooftop at Roof 106 above The Matheson. Sunset, a glass of wine, shared apps. Tough to beat.

Another night, our friends took us up to Catelli’s in Geyserville, where dinner stretched into one of those evenings where you forget you’re even dining out. It felt so comfortable, it was as if we were being served by a private chef at home. Speaking of, one night we grilled at our friends place.

If you’re craving pizza instead, Diavola is just down the street from Catelli’s.

Back in Healdsburg, Little Saint became one of my favorites. It’s an entirely vegan restaurant, bottle shop, and live music venue. As someone who generally believes butter improves most situations, I never once found myself wishing for it. Probably the highest compliment I can give.

One piece of advice. Don’t overbook yourself. We had zero reservations for any of this. Leave room for a long lunch. Wander into the bakery that catches your eye. Say yes when someone recommends a place you’ve never heard of. Some of our favorite meals weren’t memorable because they were expensive or exclusive. They were memorable because we had nowhere else to be.

Healdsburg had a funny way of convincing me that I wasn’t in a hurry. Or on a deadline. Even though I very much was and had to do a little work every morning. It wasn’t happiness that this trip brought. It was something deeper than that. Peace. Peace that when you’re with the right people in the right place, everything else works out around it.

And it has lingered with me. I brought home an ounce of that peace. A case of wine, too.