There is something special happening in South San Jose this weekend—and this year it feels particularly close to home for those of us in and around Almaden Valley.
On Sunday, September 13, Viva CalleSJ returns with a brand-new route appropriately named “Into the Valley.”
From 10 a.m. to 3 p.m., approximately six miles of South San Jose streets will be transformed into a car-free community space where people can walk, bike, skate, roll and simply enjoy the neighborhoods around them.
And the best part?
This isn't a race.
There is no starting line or finish line. You can enter the route wherever you'd like, travel as much or as little as you want, and experience South San Jose at your own pace.
Viva CalleSJ Comes South
Viva CalleSJ has spent the past decade transforming San Jose streets into temporary public spaces designed around people rather than cars.
But the September event is particularly interesting for South San Jose residents.
The new “Into the Valley” route stretches through an area rich in both neighborhood character and Santa Clara Valley history.
Three major activity hubs anchor the route:
Martial Cottle Park
De Anza Park
Cahalan Park
Each hub will feature free activities, entertainment and community fun.
Along the route, visitors can also expect vendors, live music and food trucks.
Whether you arrive on two wheels, roller skates, on foot or pushing a stroller, the idea is simple: get outside and experience the community from a completely different perspective.
Martial Cottle Park: A Connection to the Valley's Past
One of my favorite parts of this year's route is Martial Cottle Park.
Today we think of Silicon Valley as one of the world's great technology centers, but it wasn't that long ago that this region was known as the “Valley of Heart's Delight.”
Orchards and farms once stretched across much of the Santa Clara Valley.
Martial Cottle Park preserves an important piece of that agricultural heritage.
The Cottle family's connection to this land reaches back to the 1800s, and generations of the family farmed the property.
That history makes Martial Cottle a perfect anchor for an event celebrating South San Jose.
It provides a wonderful reminder that underneath today's Silicon Valley is a community with deep agricultural roots.
A Different Way to Experience South San Jose
One reason I love events like Viva CalleSJ is that they allow us to experience familiar neighborhoods differently.
Normally, we drive through these streets.
On Sunday, we'll be able to slow down.
Walk them.
Bike them.
Stop and talk with neighbors.
Visit a local business.
Listen to music.
Grab something from a food truck.
Let the kids explore.
And simply enjoy being outside.
That's a very different experience from seeing South San Jose through a windshield.
Why This Feels So “Almaden”
Viva CalleSJ also highlights something I've talked about frequently when discussing the Almaden Valley lifestyle.
People aren't choosing homes based solely on bedrooms, bathrooms and square footage.
They're choosing communities.
Access to parks matters.
Trails matter.
Open space matters.
Outdoor recreation matters.
Neighborhood connections matter.
And having places where families can spend time outside together matters.
Almaden Valley and the surrounding South San Jose neighborhoods offer an unusual combination: access to Silicon Valley while still providing proximity to parks, trails, hills and outdoor recreation.
Viva CalleSJ puts many of those qualities front and center.
You Don't Need a Bike
Don't let the “open streets” concept make you think this is strictly a cycling event.
It isn't.
You can walk.
Jog.
Rollerblade.
Skate.
Bring the kids.
Walk the dog.
Stop for a picnic.
Listen to entertainment.
Visit the activity hubs.
Or simply wander around and enjoy the atmosphere.
You also don't have to complete all six miles. There is no official beginning or end, so you can join wherever it's convenient and stay for as long as you'd like.
What to Know Before You Go
Viva CalleSJ: Into the Valley
Sunday, September 13, 2026
10:00 a.m. – 3:00 p.m.
South San Jose
Approximately 6-mile car-free route
Activity Hubs:
Martial Cottle Park
De Anza Park
Cahalan Park
Admission:
FREE
Bring:
Comfortable shoes, sunscreen, a reusable water bottle and a helmet if you're riding.
Participants under 18 who are riding bicycles are required to wear helmets.
Free water is available at hydration stations at the activity hubs, and portable restrooms—including ADA-accessible facilities—are available along the route and at the hubs.
Parking may be limited because of street closures, so event organizers recommend using VTA when possible.
More Than an Event—It's a Look at the South San Jose Lifestyle
It's easy to talk about lifestyle when discussing real estate.
Events like Viva CalleSJ actually let us experience it.
A strong community isn't defined only by its houses.
It's the parks where neighbors meet.
The trails where people spend Saturday mornings.
The local businesses people support.
The outdoor spaces where children grow up.
And events that bring thousands of people together simply to enjoy where they live.
That's one reason South San Jose—and particularly the greater Almaden area—continues to offer such an appealing lifestyle.
We have access to one of the world's most dynamic economic regions while still being surrounded by reminders of the valley that existed long before Silicon Valley.
On Sunday, Viva CalleSJ gives us an opportunity to slow down and enjoy a little bit of both.
I'll see you “Into the Valley!”
EVENT QUICK GUIDE
Event: Viva CalleSJ — Into the Valley
Date: Sunday, September 13, 2026
Time: 10:00 a.m.–3:00 p.m.
Location: South San Jose
Cost: FREE
Route: Approximately 6 miles
Featured Hubs: Martial Cottle Park, De Anza Park and Cahalan Park
Best For: Families, cyclists, walkers, runners, dog walkers, outdoor enthusiasts and anyone who wants to explore South San Jose.
Official Information & Route Map:
VivaCalleSJ.org