Sometimes the best things are right under your nose—or in this case, right off Sonoma’s historic plaza. Enjoy a 2.5-mile (round-trip) sunset hike on Sonoma’s Overlook Trail. Locals have long 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 (though you certainly can): The hike starts and ends just a few blocks off Sonoma’s town square. The trail gently ascends through blue oaks, manzanitas, and madrones. In the spring, it’s decorated with buttercups, mule ears, sky lupine, and royal larkspur. On hot days, oak-shaded benches make a nice break spot.
You’ll wind your way up Schocken Hill, with views of Mount Tamalpais, San Pablo Bay, and even San Francisco on a clear day. Sunset-watching here is sublime from the stone bench marking the top of the hill. Finish the loop and take the five-minute stroll back to Sonoma Square.
BONUS FIRE PIT & WINE: After your late-day hike, get down to the plaza for some fireside chatting and pinots at Roche Winery (open until 7:30 p.m.). Their garden patio also has food pop-ups. Or head to dinner at any of the surrounding restaurants.
TIP: Every Tuesday from May through September, Sonoma Valley’s historic plaza is home to a lively locals’ favorite Farmers’ Market beginning at 5 p.m. Bring your own picnic (wine is allowed) and pick up fresh locally sourced fruits and vegetables, plus artisan goods. There are food trucks too!
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. There’s a small parking lot at the trailhead. No dogs.