Sometimes the best things are right under your nose—or in this case, right off the square. Start the day with a 2.5-mile (round-trip) hike on Sonoma’s Overlook Trail. Since 2002, locals have been enjoying this backyard park that offers an expansive panorama of Sonoma Valley and its cascading green hills and vineyards. There’s no need to drive to this trailhead: The hike starts and ends just a few blocks off Sonoma’s central square. The path gently ascends through blue oaks, manzanitas, and madrones. In the spring, the trail is decorated with buttercups, mule ears, sky lupine, and royal larkspur. On hot days, oak-shaded benches make a nice break spot. The trail winds up Schocken Hill with views of Mount Tamalpais, San Pablo Bay, and even San Francisco on a clear day. Finish the loop and take the five-minute stroll back to Sonoma Square.
To reach the trailhead from the square, head north on First St. West. Find the staging area just beyond the Veterans Memorial Building on the right side of the street. Follow the signs for the Overlook Trail’s Upper Loop Trail. No dogs.