Upcoming South Bay events

Purchase tickets now the Food and Wine Stroll on August 23.

Whether you’re looking for a concert, volunteer opportunities, great food and drinks, or community markets this weekend, the South Bay has got you covered. Check out some of these local events below!

Updated September 23, 2021

Live on Main: A Free Summer Concert Series

19401 Stevens Creek Blvd

September 24, 6:30 p.m. to 8:30 p.m.

Bring a lawn chair or blanket and enjoy Cupertino’s last Live on Main concert of the summer. The series will be closing out with a performance by the Cisco Kid. Meals will be available to-go from local eateries. Learn more here.

Cupertino’s 8th Annual Fall Bike Fest

City Hall, 10300 Torre Ave, Cupertino

September 25, 9 a.m. to 1 p.m.

This Saturday, head to City Hall to enjoy a bike rodeo, family bike ride, helmet fittings, bike safety and reliability checks, bike mechanics, bike clinics, art and poetry, and so much more. You can find the even details here.

Posted September 17, 2021

Coastal Cleanup Day

San Jose (Address provided following registration)

September 18, 9 a.m. to 12 p.m.

Celebrate the earth and our beautiful community by volunteering to cleanup our trails and creeks. In order to participate, complete a City of San Jose Waiver prior to the event. Community service hours are available! Register and learn more here.

Los Gatos 25th Annual Art & Wine Festival, Fiesta de Artes

Civic Center Lawn, 110 E Main Street, Los Gatos

September 18 and 19, 10:00am to 6:00pm

The Los Gatos Art & Wine Festival, Fiesta de Artes, features over 200 artists, fine wines, beer, and live music by the hottest local bands around. Admission is free! Brought to you by the Kiwanis Club of Los Gatos as their biggest fundraiser of the year – all proceeds go right back into the community- from scholarships, to Special Games for special needs youth in Santa Clara County, and more. For more information visit www.losgatosfiesta.com .

San Jose Bacon and Beer Classic 2021

Excite Ballpark, 588 E Alma Ave, San Jose

September 18, 11 a.m. to 8 p.m.

This Saturday, Excite Ballpark will be filled with local breweries, gourmet bacon dishes, and flavorful Hormel Black Label bacon strips. Timeslots are selected to create a seamless one-way tasting trail. Try over 50+ beers and ciders, 7 bacon entrees, and 2 sweet treats. You can reserve your timeslot here.

Willow Glen Fall Wine Walk 2021

Downtown Willow Glen, Lincoln Ave, San Jose

September 18, 2 p.m. to 5 p.m.

Head downtown this weekend for a walking wine-tasting tour. Over 24 local wineries will be included on the tour. The event will occur rain or shine! You can purchase your tickets here.

Sounds of Summer Music Series

Santana Row, San Jose

September 21, 6 p.m. to 8 p.m.

Every Tuesday through September, enjoy live music in Park Valencia. This Tuesday features county singer Toree McGee. No tickets necessary, just head on downtown! More information is available here.

2021 Cupertino Night Market

De Anza College, 21250 Stevens Creek Blvd, Cupertino, CA

September 25, 3 p.m. to 10 p.m.

Hosted by the Cupertino Chamber of Commerce, The Cupertino Night Market is an open-air market with street food, snacks, retail, and live entertainment. Admission and parking is free! If you’re a vendor looking to participate, you can register here.