Simply Sunsational!

Hike Sonoma Valley's Overlook Trail at Sunset

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.

Trending Stories NorCal

View all Stories
  1. Mike Zakowski (aka Mike the Baker) standing in front of his wood-fire oven at the Sonoma Valley Farmers' Market

    NEW! Walkin' and Talkin': Break Bread, Go On a Panoramic Hike

    What’s a world-traveling, medal-winning baker’s favorite local hike? Weekend Sherpa co-founder Brad Day caught up with Mike Zakowski (aka Mike the Baker) at Sonoma’s Friday farmers' market, where his wood-fired loaves draw loyal crowds. Between bites of fresh-baked bread, they talk baking, travel, and why Sonoma's Overlook Trail is one of his favorite quick, panoramic hikes.

    View
  2. Hidden Botanical Garden

    Forget a dozen roses. Give your love a botanical garden. Hidden on the western slope of Sonoma Valley’s Mayacamas Mountains, Sonoma Botanical Garden has one of the Bay Area’s best displays of Asian flora—and it’s a brilliant place for a quiet picnic and some calming contemplations.

    View
  3. Sunnyvale and Salty

    For up-close bird watching, it’s hard to beat a walk along the San Francisco Bay. This 5-mile loop on the Sunnyvale coast is a favorite of local wildlife photographers.

    View
  4. A man takes a break at a temple spot on a hike at Dragon Mountain in Milptas

    Dragon Quest

    The newly reopened, 4-mile out-and-back hike at Dragon Mountain in Milpitas mixes the physical with the spiritual for a serene hiking experience.

    View

Trending Stories SoCal

View all Stories
  1. Sponsored

    Warm Up to Winter in Reno Tahoe

    2026 is just getting started, but there’s one place already rising to the top as the best for adventure and relaxation: Reno Tahoe. The awe—and ahhhs—begin as soon as you arrive. G

    View
  2. A woman stands at Dante's View in Death Valley, looking out to Telescope Peak and Manly Lake, Badwater Basin below.

    Sunset Hike at Dante's View

    It’s one of the world’s best places to watch a sunset. Dante’s View is a 5,476-foot vantage of the whole southern basin of Death Valley from the top of the Black Mountains. Right now there's a banner and bonus view of a rare lake formation that appears only after big rains.

    View
  3. It's a Waterfall Life

    Tahquitz Canyon’s crystalline stream and lush stands of desert lavender, honey mesquite, and leafy sycamores is home to an easy day hike with a big bonus: a 60-foot waterfall that runs with remarkable gusto after winter rains.

    View
  4. Oh Snow Nice

    Live in California long enough, and you’ll come to know the rite of passage called “going to the snow”–when we ditch our fair-weather cities and towns in search of winter weather. Sequoia & Kings Canyon National Parks deliver a winter wonderland worth a visit if there’s been a good dose of snow.

    View