Spring 2026 in the Valley: Your Guide to Events in Los Gatos and Saratoga
March 5, 2026
March 5, 2026
As the winter chill fades and the hillsides of the Santa Cruz Mountains turn a vibrant, mossy green, there is no better place to be than the South Bay. The "shoulder season" in Los Gatos and Saratoga isn't just a change in weather—it’s a total cultural awakening. From the high-energy cyclocross of the Cat’s Hill Classic to the sophisticated, world-class acoustics of the Mountain Winery’s opening nights, the 2026 spring season is shaping up to be one for the books.
Whether you’re a local looking to rediscover your backyard or a visitor hunting for that perfect glass of Chardonnay in a historic village, this three-month guide captures the very best of our community’s spirit. Dust off your walking shoes and grab your sunglasses; here is what’s happening in Los Gatos and Saratoga from March through May.
March 7: Police Foundation Officers Ball (Los Gatos) – A black-tie fundraiser at Testarossa Winery with dinner and jazz.
March 7: Let’s Work Saratoga! (Saratoga) – Community volunteer day at Quarry Park (9:00 AM – 12:00 PM).
March 8: International Women's Day Celebration (Los Gatos) – Participating shops and restaurants downtown will host festivities marked by colored balloons.
March 14: St. Paddy’s Party in the Village (Saratoga) – Festive celebration in the Historic Saratoga Village (2:00 PM – 4:00 PM).
March 15: Mad Hatter’s Tea (Saratoga) – A whimsical tea party at Montalvo Arts Center with seatings at 11:30 AM and 2:30 PM.
March 19: Carnegie Library History Tour (Los Gatos) – Hosted by NUMU (New Museum Los Gatos) at 11:00 AM.
March 21: Cat’s Hill Bike Race (Los Gatos) – One of the most famous (and steepest) bicycle races in the U.S., held in the Almond Grove neighborhood.
March 28: Chamber of Commerce "Shine Among the Stars" Gala (Los Gatos) – The first full-scale gala in six years, held at Nestldown.
March 28: The High Kings (Saratoga) – Live performance at Montalvo Arts Center’s Carriage House.
April 5: Hike & Meditation Pop-up (Saratoga) – A guided outdoor wellness session at Villa Montalvo.
April 9–11: Performance Series at Montalvo (Saratoga) – Featuring Las Cafeteras (Apr 9), Marshall Crenshaw (Apr 10), and comedian Kira Soltanovich (Apr 11).
April 25: Spring Wine Walk (Los Gatos) – Sip local wines while exploring the boutiques of Downtown Los Gatos.
April 26: Spring into Green (Los Gatos) – The town’s combined Earth Day and "Keep Los Gatos Beautiful" celebration at Town Plaza Park, featuring the Farmers Market and eco-booths.
April 29–30: Ukulele & Island Music (Saratoga) – The Makaha Sons (Apr 29) and the Ukulele Orchestra of Great Britain (Apr 30) at Montalvo.
May 7: Scotty McCreery (Saratoga) – Country music kicks off the season at The Mountain Winery.
May 9: Spring Wine Stroll Experience (Saratoga) – Taste wines from local vintners throughout the Historic Saratoga Village (2:30 PM – 5:30 PM).
May 9: George Benson (Saratoga) – Legendary jazz performance at The Mountain Winery.
May 10: Seal (Saratoga) – A special Mother’s Day concert performance at The Mountain Winery.
May 15: Chelsea Handler (Saratoga) – Live comedy at The Mountain Winery.
May 17: Saint Michael Trio: Spring Fling (Saratoga) – Classical performance at the Carriage House Theatre.
May 19: Jason Bonham’s Led Zeppelin Evening (Saratoga) – High-energy rock at The Mountain Winery.
Los Gatos Farmers Market: Every Sunday (9:00 AM – 1:00 PM) at Town Plaza Park.
Saratoga Farmers Market: Every Saturday (9:00 AM – 1:00 PM) at West Valley College.
NUMU (New Museum Los Gatos): Monthly rotating "First Thursday" crafts and weekend history talks.
From the intimate gallery talks at NUMU to the grand-scale comedy and rock sets overlooking the valley at the Mountain Winery, the next few months offer a perfect blend of small-town charm and big-city talent. These events often sell out quickly—especially the wine walks and the Mother’s Day specials—so we recommend securing your tickets and making dinner reservations well in advance.
No matter which dates you circle on your calendar, we hope you take a moment to enjoy the blossoms, the local vintages, and the vibrant community that makes Los Gatos and Saratoga so unique. Bouja & Swenson Group will see you out in the sunshine!
Are you planning a move to the area this spring? Would you like a private tour of any of these neighborhoods before the spring season kicks into high gear? Contact us for all of your real estate needs!
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