You’re in Sonoma, tasting some wine, feeling pretty good—now you want to enjoy a short hike to take in the views of the valley. Where to go? The answer is just north of Sonoma’s historic plaza. The Overlook Trail is a local favorite. The 1-mile (one-way) hike to reach the “overlook” is a gentle grade among meadows, grasslands, and oak trees.
The viewpoint is marked by rock-benches, one of which has a small plastic container holding a pen and log-book … go ahead, write something cheesy! The pinnacle viewpoint is known as the west slope of Shocken Hill, where a plaque lists out in detail the sweeping view before you.
Bask in a vista spanning the town of Sonoma, its valley, and—on clear days—Mount Tam and San Francisco. And don’t be startled by deer; they like the view up here too. Enjoy the moment. It’s a short jaunt down from this Sonoma stunner.
PIZZA BONUS: Family owned and run since 1959, Mary’s Pizza Shack restaurant on the historic Sonoma Plaza is a good old-fashioned classic. True to its Italian heritage, the food is made from scratch with quality ingredients: we’re talking traditional family-recipe pizzas, pastas, pesto, and more. Their neighboring Slice Shack by Mary’s is a quick-stop shop to grab a slice on the go, or some of their famous meatballs (they’ve also got salads and wine and beer). You can take your food across the street to a picnic table at the Sonoma Plaza where you can also (legally!) drink your adult beverages.
To reach the trailhead from Sonoma Plaza, head north on First St. West. Find the staging area just beyond the Veterans Memorial Building on the right side of the street (map). Follow the signs for the Overlook Trail’s Upper Meadow Loop trail. Give yourself 30 minutes to reach the top. No dogs.