August has a way of making the Bay Area feel like one big summery playground. Warm days invite us outdoors, while cooler evenings set the stage for concerts in the park, wine festivals, and unforgettable community events.
Whether you’re watching talented pups ride the waves in Pacifica, admiring spectacular collector cars in Monterey, or simply escaping to the coast for a refreshing ocean breeze (try a Duffy outing!), there are countless ways to savor the season.
Here are a few of my favorite August adventures. I hope to see you out there!
World Dog Surfing Championships | Pacifica | Aug. 1
Calling all dog lovers! Come see some serious dog surfing talent hang ten and compete for the Golden Surfie Medal on the waves at Linda Mar Beach. Explore the Surf Dog Village for swag and gear, and enjoy a dog disc competition, costume contest, and yappy hour after the show. It’s free to the public, but please consider making a donation to the associated charities. Learn more at surfdogchampionships.com.
Watsonville Strawberry Festival | Watsonville | Aug. 1-2
Celebrate the Pajaro Valley’s largest crop in historic downtown Watsonville! Saturday morning kicks off with the Strawberry Jam 1K and 5K Fun Run/Walk, then enjoy unique strawberry foods, carnival rides, live music, arts & crafts, and—of course—a pie-eating contest! For more info, click here.
Music In The Park | Downtown Los Gatos | Aug. 2, 9, 16, 23
Pack a picnic and enjoy a relaxing afternoon with friends and family at Los Gatos Civic Center Park listening to live music every Sunday through Aug. 23. More info here.
Summer Concert Series | Downtown Campbell | Aug. 6, 13, 20, 27
Bring a lawn chair and chill out every Thursday evening through Aug. 27 at Campbell’s free Summer Concert Series, featuring Latin favorites to classic and contemporary rock at Orchard City Green. More info here.
Monterey Car Week & Pebble Beach Concours d’Elegance | Monterey & Pebble Beach | Aug. 7-16
Car lovers head to Monterey every August for this can’t-miss event featuring classic car shows, luxury automobiles, vintage racing, and so much more. On August 16, watch style icons, innovative prototypes, and racing greats compete for the top prize in the collector car world at the 75th Concours d’Elegance on the famed 18th fairway at Pebble Beach, a tradition going back over half a century. For more information, visit seemonterey.com.
San Jose Jazz Summer Fest | Downtown San Jose | Aug. 7-9
Patti LaBelle, the Godmother of Soul, headlines this year’s San Jose Jazz Summer Fest, bringing serious company and pure electric energy to the heart of downtown San Jose. Hear from world-class jazz, funk, R&B and Latin greats, including Trombone Shorty & Orleans Avenue, Zapp Ft. Tuxedo, Afro-Cuban All Stars, Cory Wong, and many others. Three days, 100+ acts, eight stages – so get your early bird passes now! Visit summerfest.sanjosejazz.org.
Fine Art In The Park | Los Altos | Aug. 8-9
Explore original, juried art from over 150 artists under the beautiful redwoods of Lincoln Park at the 51st Annual Fine Art in the Park in Los Altos. Enjoy delicious food, wine, and live music while you search amongst photography, oil paintings, watercolors, sculpture, ceramics, and jewelry for treasures for your home, garden, or office. For more info, visit rotaryartshow.com.
Guglielmo Winery Harvest Festival | Morgan Hill | Aug. 15
Experience an unforgettable evening in the vineyards at the 32nd Annual Harvest Festival Celebration at Guglielmo Winery as it celebrates 101 years of family winemaking tradition. Enjoy award-winning wines, a delicious harvest dinner, live music, and traditions like the grape stomp that have generations of family, friends, and wine-lovers coming back year after year. For tickets and more info, visit guglielmowinery.com.
Santa Clara County Fair | Santa Clara | Aug. 19-23
Get fired up to attend the 82nd Annual Santa Clara County Fair! Prepare for family-friendly entertainment, thrilling carnival rides, classic fair food, extreme shows, and 4-H exhibits celebrating our vibrant community. Get your tickets here.
