My husband and I are staying in Healdsburg in June for the Sonoma Valley portion of our San Francisco/Wine Country trip.
First, if you're a local, dress up is a long sleeve shirt and your dress jeans; nice pair of shoes or dress boots. So, just keep that in mind while packing.....
About a 45 minue drive from Healdsburg in the Redwwods is Union Hotel....great casual restaurant to go to.
417 Healdsburg Avenue
Manzanita or Zin are worth a look.
I enjoyed Willi's. Sort of upscale brewpub type food. Excellent oysters - fun spot since food is mostly meant to be shared dishes.
I also ate at Cyrus - excellent but not casual.
Even in Cyrus - I suspect one of the dressier spots in town there were some formally dressed people and others in khakis & tropical shirts.
Mini is right that you'll feel comfortable in nice jeans and shirt virtually everywhere in Healdsburg, with the possible exceptions of Cyrus and Madrona Manor, but even Cyrus has a bar menu where you can sample some of their wonderful cuisine in a casual atmosphere. As a rule, the earlier you dine, the more casually dressed are the diners. From 8pm on, particularly wkends, people tend to dress up more. In-town Healdsburg, you'll have a large array of very casual places to dine or buy picnic items, inc: Center Street Cafe and Deli (304 Center), Oakville Grocery (124 Matheson), Costeaux French Bakery ( 417 Healdsburg Ave.), Ravenous Cafe (420 Center St.), Bear Republic Brewing Co. (345 Healdsburg Ave.), Lotus Thai Restaurant (109 Plaza St.), diVine Pizza (1051 Vine St.), and Bovolo Cafe (106 Matheson St.) in the Plaza Farms building (which is a neat place where you can also taste wine and buy local products). I've also heard that Fitch Mountain Eddie's (1301 Headsburg Ave.) is a great spot for breakfast or lunch if you like good, basic comfort food. Maj has already mentioned one of my top favorites for a casual lunch or dinner: Willi's Seafood at 403 Healdsburg Ave. No reserv's, you just drop by. I actually like dining inside as it tends to be quieter and the artistic decor is wonderful. For most people tho', the front sidewalk patio area remains the very popular choice.
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