Your Silicon Valley Weekend, August 21–23: Air Supply on the Saratoga Hillside and a Weekend of Free Local Finds

By Brad Bell — Coldwell Banker Global Luxury — Silicon Valley native, top 1% of realtors nationally

Late August is the last full stretch of the valley’s outdoor season before the school calendar takes over. This weekend the Mountain Winery hosts a hillside show in Saratoga, a specialty fair runs all three days in Sunnyvale, and the free Sunday and Saturday standbys are all still running. Here is the plan.

Saturday Night: Air Supply at the Mountain Winery

Air Supply, The Mountain Winery, Saratoga — Saturday, August 22, 7:30 PM.

If you have never done a show at the Mountain Winery, this is the format: an outdoor amphitheater carved into the hillside above Saratoga, roughly 1,700 seats, with the entire valley spread out below you as the sun goes down. There is no bad seat and no bad view. Arrive early enough to have a glass on the terrace before the set — that hour is genuinely half the reason people go.

Practical notes: the drive up Pierce Road is narrow and slow when the lot fills, so budget more time than the map suggests. Bring a layer. The hillside cools fast after sunset even in August.

All Weekend: The Cactus and Succulent Fair in Sunnyvale

San Jose Cactus and Succulent Fair, Peterson Middle School, 1380 Rosalia Ave, Sunnyvale — Friday through Sunday, August 21–23. Admission is free.

Hours are Friday 6–9 PM (public sale), Saturday 8 AM–6 PM, and Sunday 11 AM–3 PM. More than 40 vendors bring cactus, succulents, and pottery, and there is a judged show alongside the sale — everything from tiny living stones to mature specimen cacti.

This is one of those long-running South Bay events that locals either attend religiously or have never heard of. Growers and collectors bring specimens you will not find at a garden center, and the pricing runs from a few dollars for a starter to serious money for a mature specimen.

It is also quietly practical if you own here. Drought-tolerant, low-water landscaping is one of the better-returning curb appeal investments in this climate, and this is the best single place in the South Bay to see what actually thrives in a Santa Clara County yard before you commit to a planting plan.

Saturday Morning: The Markets

The Saturday market circuit is the most reliable thing on the valley calendar, and late August is peak season for it — stone fruit, tomatoes, melons, and corn are all at their best right now.

• Sunnyvale Farmers Market — downtown at the plaza, Saturday morning. The largest of the local Saturday markets and an easy walk from Murphy Avenue.
• Santa Clara Farmers Market — Saturday morning, a solid neighborhood market with less crowding than Sunnyvale.
• Campbell Farmers Market — Sunday morning on Campbell Avenue, and one of the most pleasant downtown settings in the valley for it.

Please confirm current hours on the market’s own site before you go — late-summer schedules occasionally shift.

Sunday: Free Music in Los Gatos

Music in the Park, Los Gatos Civic Center lawn — Sunday, August 23, 5–7 PM. Harry and the Hitmen. Free.

The series has run in Los Gatos since 1988 and this is one of the last dates of the 2026 summer schedule. It is one of the genuinely great free things in this valley: bring a blanket, bring dinner, and let the kids run.

If you are looking for a lower-key Sunday, the Los Gatos Creek Trail and Vasona Lake County Park are both at their best in late-summer evening light, and Fremont Older Open Space above Saratoga gives you the valley view without the drive to the coast.

What This Weekend Says About Where You Live

Every weekend guide I write comes back to the same underlying point, because it is the thing buyers most consistently underweight: proximity to this stuff is a real and measurable component of value in Silicon Valley.

Walkability to a downtown like Los Gatos, Campbell, Sunnyvale, or Saratoga Village is priced into the market here, and it holds through cycles better than almost any other feature buyers pay for. A home ten minutes from a Saturday market and a Sunday concert lawn lives differently than one that requires a car for everything — and the market knows it.

If weekends like this are the reason you want to be in a particular part of the valley, that is a legitimate input into where you buy. It belongs in the conversation alongside price, schools, and commute.