Montgomery Hill Park

A Hill With History

Perched above Evergreen Valley College, this park is named after John Joseph Montgomery, not just any aviator, but a true pioneer who tested and launched his gliders here in the early 1900s. As you wander the grounds, you'll spot historical placards that tell the story of Montgomery's flights and his contributions to aviation - a little piece of history right in San Jose.

Majestic oak tree spreads its branches over the rolling hills

Photo: kjardin@pacbell.net (CC BY-SA 2.0)

Trails to Explore

The park offers about 0.4 miles of unpaved trail stretching from Evergreen Creek/Falls Creek Road all the way to Yerba Buena Road. If you're feeling ambitious and want to tackle the entire system, you'll cover about 0.75 miles through a figure-eight pattern with multiple loops.

The trails wind through natural grasslands and oak trees, giving you a genuine taste of the local ecosystem. And if you're up for more, the park connects to Evergreen Creek, adding another 1.2 miles to your journey.

These wide trails are genuinely inclusive - comfortable for both hikers and cyclists to share the space without constantly dodging each other.

Want to reach the summit? You've got options. Choose the short, steep route (about 0.125 miles) if you're looking for a quick cardio burst, or take the more gradual path for a leisurely climb that's easier on the knees.

Nature's Showcase

If you can visit in spring, do it. That's when wildflowers and wild mustard transform the landscape with splashes of color. After the rainy season, these hills shift dramatically from brown to a vibrant green that feels almost surreal.

The rolling terrain and quiet woodlands make for a great quick nature escape, even when you don't have time for a full-day hike. Keep your eyes open and you might spot various birds or even coyotes lingering near the tree lines.

The highlight, though? Those panoramic views. From up here, you can see the entire San Jose metropolitan area, the Santa Cruz Mountains, and the East Bay hills stretching out before you. If you time it right, the sunset views are worth the climb - the way the light bathes the valley in golden hues is quite beautiful.

Trees and grassland in Montgomery Hill Park

Photo: kjardin@pacbell.net (CC BY-SA 2.0)

Beyond Just Hiking

This isn't just a hiking spot. During fall, you'll likely see cross-country runners training on these challenging hills - local high school teams often use the terrain for races.

On breezy days, the open hilltops create perfect conditions for kite flying, turning the sky into a colorful canvas of dancing kites.

And if you're into mountain biking, especially as a beginner or intermediate rider, these rolling hills offer a fun challenge with slopes that can reach up to a 20% grade - enough to get your heart pumping without being overly technical.

Westward view across a solar panel array toward San Jose

Photo: kjardin@pacbell.net (CC BY-SA 2.0)

Good to Know

After your trek, you can relax at one of the picnic tables located at the bottom of the hill. You'll also find benches thoughtfully placed along the trails where you can catch your breath while soaking in those views.

Just note that there are no restroom facilities on the trails, so plan accordingly. During summer, the area gets pretty hot and dry with minimal shade, so bring plenty of water and sun protection - your future self will thank you.

The park is dog-friendly, but do keep your furry friends leashed. One heads-up for pet owners: during dry seasons, watch out for foxtails along the trails that can cause problems for curious pups.

In the Neighborhood

While you're in the area, check out the Montgomery Hill Observatory on the grounds of Evergreen Valley College - a fitting neighbor that continues the park's connection to science and discovery.

Traveling with kids? The nearby Fowler Creek Playground offers a wonderful spot for little ones to burn off extra energy after exploring the trails.