Healdsburg is charming. Every brick, every flower box, every elegant shop and eclectic gallery, every five-star restaurant and cozy cafe on every single corner speak to this town’s genuine individuality and down-to-earth-treasures. Downtown Healdsburg may be surrounded by bucolic rolling hills and picturesque vineyards, but around this age-old square, its hard to imagine being anywhere else more delightful. No matter what time of year, Healdsburg is a town for every season.