San Jose Jazz Summer Fest
2025-08-10 10:00 - 19:00 (America/Los_Angeles) | Plaza de Cesar Chavez, 1 Paseo de San Antonio, San Jose, CA, 95113
One of the biggest music events in Silicon Valley! San José Jazz Summer Fest brings together top artists in jazz, blues, R&B, funk, Latin, and soul for a weekend of nonstop music across multiple stages. With food vendors, beer and wine gardens, and family-friendly programming, this festival attracts thousands each year for its high energy and diverse musical talent.
The festival runs over at Plaza de César Chávez Park in downtown San Jose:

Friday, August 8, 2025: 4:00 PM – 9:30 PM
Saturday, August 9, 2025: 10:00 AM – 8:30 PM
Sunday, August 10, 2025: 10:00 AM – 7:00 PM

Los Gatos Music in the Park
2025-08-10 17:00 - 19:00, 2025-08-17 17:00 - 19:00, 2025-08-24 17:00 - 19:00 | Los Gatos Civic Center Lawn, 110 E Main St, Los Gatos, CA
Relax on the lawn with family, friends, and a picnic while enjoying free live music every Sunday in August. This beloved local series features everything from funk and soul to classic rock and Americana. The lineup includes bands like Wolf Jett, Ideateam, and Freestone Peaches. It’s a perfect way to wind down the weekend in a scenic downtown setting.

26th Annual Sunnyvale Summer Series Music & Market
2025-08-13 18:00 - 20:30, 2025-08-20 18:00 - 20:30, 2025-08-27 18:00 - 20:00 | Downtown Sunnyvale, 192 S. Murphy Ave., Sunnyvale, CA, 94086
Transform Wednesday nights into your weekly summer ritual with this vibrant music and market series. Stroll through Sunnyvale's downtown, sip local brews, browse artisan booths, and relax to live performances under string lights. It’s the perfect midweek chance to unwind, connect with friends, and support local makers—all in a lively, safe outdoor atmosphere. For more information, click here.

Concerts on the Plaza
2025-08-15 18:00 - 19:30, 2025-08-22 18:00 - 19:30, 2025-08-29 18:00 - 19:30 | Civic Center Plaza, 500 Castro Street, Mountain View, CA, 94041, United States
Concerts on the Plaza is a free summer music series hosted at Civic Center Plaza (500 Castro Street) in downtown Mountain View. In 2025, the event returns with sixteen live performances held Friday evenings from 6:00–7:30 p.m., running weekly from June through September.
Each week features a different band spanning styles like Pop/R&B/Rock, Classic Rock, Jazz-Funk, Latin tribute, and more—creating a fun, dance-friendly atmosphere for families, friends, and neighbors. The series combines lively music, community spirit, and outdoor enjoyment—perfect for making summer memories together.
Jun 6 — Vybe Society (Pop / R&B / Rock)Jun 13 — Livewire (’70s & ’80s Rock / Dance Hits)Jun 20 — The Real Thang (’60s–’80s Rock / Funk)Jun 27 — Misspent Youth (Classic Rock)
Jul 4 — No Performance (Holiday)Jul 11 — East Side Funk (Original Jazz-Funk)Jul 18 — Daze On the Green (Party Cover Band)Jul 25 — Dolce Musica (R&B / Soul)
Aug 1 — Sounds of Selena (Latin Tribute Dance Band)Aug 8 — RPM Band (Rock ’n’ Roll Dance Music)Aug 15 — The China Cats (Grateful Dead Tribute Band)Aug 22 — The Houserockers (Rock & Soul Band)Aug 29 — False Bottom Band (Bluegrass / Rock / Country)
Sep 5 — The Peelers (Latest Hits Cover / Mashup Band)Sep 12 — Fog City Swampers (CCR / Rock)Sep 19 — The Wanderers (Classic / Modern Dance Rock)Sep 26 — The Drifting Cowboys (Hank Williams Tribute Band)

Palo Alto's Family Movie Night Series
2025-08-15 19:00 | Mitchell Park Athletic Field, 600 East Meadow Dr, Palo Alto, CA
This free outdoor movie night is a Palo Alto summer tradition! Gather with neighbors and bring your blankets and lawn chairs for a cozy evening under the stars. August 1 features Mufasa, and August 15 features The Wild Robot. Seating opens at 7 PM, so arrive early to grab your spot and enjoy a family-friendly atmosphere. No registration required—just show up and enjoy! The movie starts at sunset (~8:00 PM).

Jane Austen’s Emma
2025-08-16 19:00 - 21:30, 2025-08-17 19:00 - 21:30, 2025-08-21 19:00 - 21:30, 2025-08-22 19:00 - 21:30, 2025-08-30 19:00 - 21:30, 2025-08-31 19:00 - 21:30 | Sanborn County Park, 16055 Sanborn Rd, Saratoga, CA
Experience a fresh take on Jane Austen’s Emma—outdoors and under the redwoods! Presented by Silicon Valley Shakespeare, this clever adaptation balances romance and wit in a serene natural amphitheater. Perfect for a date night or family outing, the show runs on select evenings throughout August. Bring jackets, snacks, and your sense of adventure.

Kings Mountain Art Fair
2025-08-30 08:00 - 17:00, 2025-08-31 08:00 - 17:00, 2025-09-01 08:00 - 17:00 | Kings Mountain Art Fair, 13889 Skyline Blvd. (Highway 35), Woodside, CA, 94062
Since 1963, this Labor Day weekend gem has brought fine arts and crafts into the redwoods. Featuring jury-selected artists, kids activities, food, and volunteer-run vibes, all proceeds support the local fire brigade and elementary school. For more information, click here.

Millbrae Art & Wine Festival
2025-08-30 10:00 - 17:00, 2025-08-31 08:00 - 17:00 | Downtown Millbrae, Broadway Ave (between Victoria Ave & Meadow Glen Ave, Millbrae, CA
A lively end‑of‑summer street fair, the Millbrae Art & Wine Festival transforms downtown Broadway into a vibrant hub of live music, local art and crafts, food, wine, beer, and family-friendly activities. Admission is free, making it a beloved Labor Day Weekend tradition in the Bay Area.
For more details—including exhibitor or sponsorship info—visit the official page Millbrae Art & Wine Festival 2025.

California’s Great America Labor Day Weekend Celebration
2025-08-30 10:00 - 22:00, 2025-08-31 10:00 - 22:00, 2025-09-01 10:00 - 22:00 | California's Great America, 4701 Great America Pkwy, Santa Clara, CA, 95054
Celebrate the end of summer at California’s Great America with a three-day Labor Day Weekend Celebration, packed with thrilling rides, entertainment, and festive fun—plus one final splash at the waterpark, South Bay Shores. On Monday, September 1, the event also features the Labor Day Car Show, showcasing vintage and classic cars throughout the park.

Lost 80’s Live at The Mountain Winery
2025-08-30 18:00 | Mountain Winery Concerts, 14831 Pierce Road, Saratoga, CA, 95070
Step into a nostalgic time machine this Saturday, August 30, 2025, as Lost 80’s Live—the longest-running 80s retro concert tour—returns to the breathtaking Mountain Winery amphitheater in Saratoga for its 10th year.
Presented by the iconic Richard Blade of SiriusXM 1st Wave, this electrifying night features a stacked lineup of A Flock of Seagulls, General Public, Big Country, The Vapors, China Crisis, The Icicle Works, Belouis Some, Josie Cotton, The Polecats, and Peter Godwin, all performing their timeless hits on one stage.
Doors open at 4pm.

Silicon Valley Pride Parade & Festival
2025-08-30 18:00 - 23:00, 2025-08-31 10:30 - 12:00 | Plaza de Cesar Chavez, 1 Paseo de San Antonio, San Jose, CA, 95113
Celebrate diversity, love, and community at Silicon Valley Pride! This two-day celebration kicks off with a night festival on Saturday and continues Sunday with the colorful downtown parade and full-day festival. Expect live music, dance performances, food trucks, family zones, drag shows, and community booths—plus plenty of joy and glitter.

Night Festival: Saturday, August 30, 2025 | 6 PM to 11 PM | Featuring Snow Tha Product
Parade: Sunday, August 31, 2025 | 10:30 AM to 12:00 PM (Downtown San Jose – Julian Street & Market Street, to Plaza de César Chávez Park)
Day Festival: Sunday, August 31, 2025 | 12 PM to 6 PM | Featuring Onya Nurve (RuPaul’s Drag Race Season 17 Winner)

BonPOP 2025
2025-08-31 14:00 - 18:00 | Celebration Garden, Golden Gate Park, San Francisco, 94122
Step into a vibrant celebration that lovingly blends tradition with inclusivity. BonPOP, hosted by KOHO and the Gardens of Golden Gate Park, invites visitors of all backgrounds to honor ancestors through joyful dance, taiko rhythms, songs, and rituals rooted in Japanese heritage. The event features vendor booths, yukata dressing experiences, lantern dedications, and community-led Bon Odori dances. For tickets, RSVP, or more info, click here.

Labor Day Cookout
2025-09-01 14:00 - 20:00 | Treehouse Hotel Silicon Valley, 1100 N Mathilda Ave, Sunnyvale, CA, 94089
Raise a glass at this ultimate Labor Day cookout—four food or drink tickets (per person) included, plus mouthwatering specials and local brews in an inviting Beer Garden setting. Mix, match, eat, and sip under the California sky. For more information, click here.
