The Best Three-Day Weekend Trips Out West: Autumn Getaways
Healdsburg, CA
Rather than trying to fit all of Sonoma or Napa Valley into a three-day trip, consider immersing yourself in Healdsburg’s local way of life by eating and drinking your way through town for 72 hours. This is one of California’s most quintessential foodie destinations, so planning your trip around restaurant reservations is always a good idea. Chef Kyle Connaughton’s three-Michelin-starred SingleThread is a Healdsburg standout, and while the multicourse California-meets-Japanese-fusion menu is a worthy bucket list meal, you can also fill your evenings with incredible dinners at chef Charlie Palmer’s Dry Creek Kitchen and Valette, both of which are Michelin-recommended.
On your first full day in Healdsburg, map out a self-guided tour of the many wine tasting rooms in the plaza. Everything is walkable, so you don’t have to worry about Ubers or designated drivers, and you can stop for bites at locally loved restaurants like Willi’s Seafood and Raw Bar or grab a pastry from 100-year-old Costeaux. For your last full day, book a couple of tastings at nearby vineyards like Bricoleur Vineyards and Mauritson Wines to connect with local producers and get a more up-close-and-personal look at the vineyards. If you’re there in the autumn, they’ll likely be undergoing the tail end of harvest.
Where to Stay:
Montage Healdsburg is the most luxurious accommodation option, and if you don’t mind making the short drive into town each day, you can’t go wrong with any of their 130 bungalow-style suites. Liora Estate offers a more convenient stay in the plaza, with an intimate setting of just 16 cozy rooms. For an even more exclusive hotel, opt for the five-room SingleThread Inn, and keep an eye out for Kyle and Katina Connaughton’s newest property opening in November 2026, The Selvedge.
