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. Keough's Hot Springs

    Soaking Up History

    When you slide into the soothing water of Keough’s Hot Springs, you’re bathing in a piece of Owens Valley history.

    View
  2. Hike to New Lights

    For an enlightening late-day hike, catch the San Francisco skyline at sunset from high atop Ring Mountain in Tiburon. This 2-mile (round-trip) hike to Turtle Rock is a perfect late afternoon wander.

    View
  3. A woman looks out to the scenery while standing next to a bench on a high point on a hike in Orinda Oaks Park in the East Bay

    Orinda Original

    This 3.5-mile out-and-back through Orinda Oaks Park and Moraga offers scenic vistas right inside the city.

    View
  4. Woman swimming in Carson Hotsprings natural thermal pool

    Hot Springs, Naturally

    Thermal spring waters are famous for their curative, relaxing elements, and Reno Tahoe is filled with them! Sink into these amazing thermal respites for a wellness super soak.

    View

Trending Stories SoCal

View all Stories
  1. Redding Ironman Whiskeytown lake
    Sponsored

    New Year, New Goal: IRONMAN 70.3 Northern California

    2026 is off and running! And swimming. And biking. Don't get left behind! Commit to one of the upcoming year’s most exciting endurance events—IRONMAN 70.3 Northern California in Redding.

    View
  2. Hikers stand atop Lassen Peak in Lassen Volcanic National Park

    Weekend Sherpa Podcast: Take It Outside

    Adventure for your earbuds. What's new in the world of the outdoors? Listen to Weekend Sherpa co-founders discuss local hikes, beaches, bike rides, camping spots and all kinds of travel and adventure in California and beyond!

    View
  3. O Enchanted Night!

    Prepare to be mesmerized! Holiday-season nights in Descanso Gardens are a magical interplay of lights and natural beauty that dazzle as you stroll through the Enchanted Forest of L

    View
  4. Hikers sitting on a large rock slab next to Three Sisters Falls in Cleveland National Forest Southern California near Julian

    Three Sisters

    Good things come in threes at this hike to a lovely trio-tiered waterfall in Cleveland National Forest. The 4.25-mile out-and-back hike rambles among rolling hills, with rocky mountain views as switchbacks take you down to a lush canyon and the falls.

    View