Mark Your Calendars – More Summer 2021 Events and Happenings

There is no shortage of fun events happening in and around Cupertino this summer, with a variety of in-person events taking place in the coming months and new ones added each week. From a Food & Wine Stroll to music festivals, there is sure to be something for everyone to be excited about this summer. We’ve rounded up a few of the events we’re looking forward to below. Have an event to add to the list? Send us a note at

Main Street Cupertino Food & Wine Stroll

For the first time since 2019, the annual Cupertino Food & Wine Stroll is back on Thursday, July 22nd from 5:30-8:30pm. There will be over 20 local food and beverage vendors participating this year so this event will be one you won’t want to miss. Tickets can be purchased at the door for $40, or for $30 through the pre-sale link here.

Mountain Winery Summer Music Series

Mountain Winery in Saratoga is hosting a wide range of musical artists this summer at their stunning property. Fans of Little Big Town, The Beach Boys, Indigo Girls, Chicago, Train and more will be excited to find their favorite artists playing at the winery venue this summer. Tickets for these artists and more can be purchased at the link here.

San Jose Jazz Summer Fest

Calling all live music lovers! The San Jose Jazz Summer Fest is bringing live music back to San Jose as one of the first major in-person music events in the Bay Area. The 3-day event will feature food, drinks and incredible music and will take place August 13–15 at the Sobrato Organization Main Stage in the Plaza de César Chavez in San Jose.

Guests can purchase a variety of ticket options, ranging from single day passes to 3-day VIP tickets. For more information and to purchase a ticket, click here.

California’s Great America- Taste of Orleans and South Bay Shores

The popular Amusement park has a lot to offer this summer, with their new water park South Bay Shores opening and the 5th Annual Taste of Orleans Festival happening each weekend from July 17th through August 1st.

The Taste of Orleans Festival will feature authentic Cajun food like alligator chowder, catfish sliders and beignets. While enjoying the Louisiana cuisine, guests will also be treated to live jazz music performances. For more information or to purchase tickets, click here.

Another great way to beat the head this summer is a visit to the newly opened South Bay Shores Water Park. From the Shark Reef Plunge to the Tide Pool, sunbathers, adventure seekers and everyone in between will find something to enjoy. For season tickets and day passes, visit the link here.

Check out more summer events for the whole family here.