Healdsburg, California

Healdsburg has just eleven thousand or so residents but despite that small package it offers an amazing historic downtown area with a world-class foodie scene, beautiful suburban neighborhoods, and finally some of the most stunning rural vineyards and farms in the country. If you choose to live in a small town but want that town to deliver an amazing lifestyle you could hardly do better than Healdsburg.

If you live in Healdsburg, at least Downtown, expect to see lots of tourists enjoying the art, food, and wine at the local spots. Is this a bad thing? Since many locals earn their living from the hospitality industry, most would argue it's a good thing. We’ll suspend judgment and simply note that plenty of locals will moan about all the tourists (and SF tech types).

Healdsburg is often described as a haven for wine lovers and a theme park for grown-ups with world-class restaurants and wineries. It is a tale of two cities as you have second-home owners and Airbnb renters mixing with long-time local families and agricultural workers. If you want a suburban family lifestyle – kids in public schools, little league and Girl Scouts, dogs, and playing in parks on weekends, then Healdsburg has that available. If on the other hand, you’re looking for a second or retirement home with lots of great wine, meals a short walk from home, and tons of downtown events and boutique experiences (and you have the money to pay for it) then Healdsburg offers that as well.

To see what locals get up to for fun in Yonkers check out the calendar of events.

We highly recommend visiting Healdsburg and staying in the community in a VRBO rather than a hotel to get a feel for living among the locals. You can receive discounted fares on travel via our partnership with Expedia as well.

Pretty much no one moves to Healdsburg to find a job. Unless you’re in the wine or farming biz. And if that’s the case then you’re probably going to live well outside the expensive city confines. Healdsburg is primarily a tourist town and so most people work in the hospitality industry or they’re wealthy tech types working remotely, or they’re empty nesters/retirees looking to enjoy the warm weather and entertaining downtown. If you’re looking for work and aren’t planning to work in wine/farming or hospitality then check out Santa Rosa, about 15 miles south.