Hike the Windy Hill Loop

San Francisco Windy Hill Open Space Preserve

Added by

Climb up the Santa Cruz Mountains for a great workout near Portola Valley with fog-permitting, views of the Pacific. Dogs are allowed on-leash. 

This 7.2-mile loop starts by heading out of the parking lot and onto the Spring Ridge Trail. Head Southeast On Spring Ridge Trail until you connect with Hamms Gulch Trail. When you jump on Hamms Gulch, head southwest for ~3.4 miles as you circle the far end of the OSP. At this point, you will connect with the Lost Trail. Head west on the Lost Trail until it connects with the Anniversary Trail, which will lead you back to Spring Ridge Trail. Once you're back on Spring Ridge, follow it until you hit your car.

The great thing about this hike is the abundance of wildflowers when in season. Out of season, it's a great place to get a longer hike in. Parts of this trail are shared use, so keep an eye for equestrians and bikers.

Also, keep in mind that the wind can really get going on Spring Ridge Trail ("Windy Hill"), so you may want to consider dressing with some warm, lightweight layers.

Pack List

  • Trail shoes
  • Athletic clothing
  • Light jacket
  • Water
  • Snacks
  • Doggie bags
Read More

Please respect the places you find on The Outbound.

Always practice Leave No Trace ethics on your adventures. Be aware of local regulations and don't damage these amazing places for the sake of a photograph. Learn More

Share

Activities:

Hiking

Skill Level:

Intermediate

Season:

Year Round

Trail Type:

Loop

Distance:

7.2 Miles

Elev. Gain:

1400 Feet

Rating:

Features:

Bathrooms
Dog Friendly
Easy Parking
Handicap Accessible
Scenic
Wildflowers

Are we missing something?

Suggest an edit

How to Get There

4 months ago

Great Hike(s)

You can do several hikes, depending on the degree of difficulty you feel like facing. Great view at the top of the hill. If you walk at a fast pace, the inclination will make it an awesome workout.

4 months ago

about 1 year ago

Beautiful!

This trail takes you through it all. You start out walking through the forest and come out on top of the mountains with a breathtaking view. Definitely worth it!

about 1 year ago

over 1 year ago

Nice Trail!

Easy to moderate hiking with gorgeous view from the windy hill summit.

over 1 year ago

Added by Ty Rauber

More Adventures Nearby

Hike the Arastradero Preserve Loop

San Francisco / Arastradero Preserve

Getting There: From Hwy 280, take the Page Mill Road exit and head West on Page Mill Road, away from Downtown Palo Alto (if you're taking 101, exit on Oregon Expressway).

Emily Schrick
1 Saves

Camp at Bootjack Campground in Mount Tamalpais State Park

San Francisco / Bootjack Campground

Bootjack Campground is located within California's Mount Tamalpais State Park.

Chris Engelsman
14 Saves

Hike through Wunderlich County Park

San Francisco / Wunderlich County Park

Located in the iconic Silicon Valley town of Woodside, Wunderlich County Park offers a number of hiking trails as well as some horseback riding trails through the wilderness.

Josh Currie
9 Saves