A super fun and easy way to get to know Healdsburg — which CNN Travel called one of the country’s “Most Romantic Small Towns” — is by taking a relaxing stroll around its plaza. You can check out the cute boutiques, explore cozy bookstores and art galleries, or just chill at a coffee shop!
Healdsburg is surrounded by three amazing wine valleys — the Alexander, Dry Creek, and Russian River — and there are even more great wine regions nearby, like Chalk Hill and Knights Valley. One of our favorite spots, Flowers Winery, is just a quick 5-minute drive from downtown. You’ll also find other awesome wineries close by, like Armida, Ferrari-Carano, Jordan, Amista, and Breathless Sparkling Wines.
About a 30-minute drive from downtown Healdsburg, Armstrong Redwoods is a beautiful 805-acre park with large California coastal redwoods. There are plenty of trails to check out, but the Armstrong Nature Trail is a popular choice if you’re visiting for the first time. It’s self-guided and has informative displays about the redwoods along the way. Another favorite is the Discovery Trail, a shorter path that takes you through the trees.