05/02/2026
Healdsburg was named the “Friendliest Small Town in California” for 2026, and for once, the hype is absolutely right.
It’s that rare spot that has small-town charm but big-city standards for food and wine - minus the pretension.
The move is to keep it simple: browse the shops around the Plaza, grab a coffee at - they’re world-class roasters who treat a morning latte like a craft science - and work your way toward a tasting.
Make sure you hit for a scoop of their heritage-inspired ice cream, like Black Sesame or Matcha, before heading to dinner at - a local favorite known for Michelin-level farm-to-table dishes served on their stunning garden patio.
If you love this Sonoma County gem as much as we do, head to the link in our bio to grab one of our Healdsburg tees and carry a bit of that small-town charm home with you.