If you're sticking around Silicon Valley for the long weekend, there's a good mix on the calendar this year: water, food, live music, and a solid pick for families with younger kids.
1. Kayaking at Lexington Reservoir, Los Gatos
Open daily, 8 AM until 30 minutes before sunset
📍 Lexington Reservoir County Park
If the weather holds up, this is where I'd start. Kayaks, canoes, and stand up paddleboards are all welcome, and every vessel needs to pass inspection before it launches. Being out on the water with the Santa Cruz Mountains all around makes it easy to forget you're minutes from the middle of Silicon Valley.
🔗 Lexington Reservoir boating info
2. Belmont Greek Festival, Belmont
Saturday and Sunday, September 5 and 6, noon to 10 PM
📍 Holy Cross Greek Orthodox Church
Come hungry. The 54th annual festival has Greek food and desserts, live music and dancing, cultural activities, shopping, and church tours. Admission is $5, $3 for seniors and teens 13 to 17, and free for kids 12 and under with an adult. There's a free shuttle running too.
🔗 Belmont Greek Festival details
3. Aimee Nolte Live at Yoshi's, Oakland
Monday, September 7, 7:30 PM
📍 Yoshi's
If you'd rather close out the weekend with dinner and live jazz, this is my pick. Doors open at 7 PM and tickets run $30 to $59. A completely different way to spend the holiday, and a great Monday night date idea.
4. Millbrae Art and Wine Festival, Millbrae
Saturday and Sunday, September 5 and 6, 10 AM to 5 PM. Free admission.
📍 Downtown Millbrae, Broadway
Now in its 55th year, this one turns downtown Millbrae into a big end of summer street fair with art, wine, food, crafts, and live music. Parking is free at Millbrae BART, with a shuttle running to the festival.
🔗 Millbrae Art and Wine Festival info
5. Kristi Yamaguchi's Family Literacy Festival, San Jose
Saturday, September 5, 9:30 AM to 4:30 PM
📍 Children's Discovery Museum
My favorite pick on this list for families with younger kids. Story readings from authors and celebrities, hands on activities, and art projects, on top of everything the museum already has going on. Special event admission is $22.
🔗 Family Literacy Festival details
One more thing: dangerous rip currents and sneaker waves are expected at the coast this weekend, so I'd skip ocean swimming and stick to the festivals. San Jose should reach the low 80s by Monday.
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See you out there! 👋
Your Realtor for Life, Anna Fine
📍 Serving San Jose, Los Gatos, Campbell, Saratoga, Sunnyvale, Cupertino, Palo Alto, Redwood City, San Carlos, Belmont, and the surrounding Silicon Valley communities