Hike the Windy Hill Loop



7.2 miles

Elevation Gain

1400 ft

Route Type


Added by Ty Rauber

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.

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Know for

Dog Friendly
Easy Parking
Handicap Accessible



Leave a Review

🥇Top Contributor

9 months ago

Great hike!

Excellent hike and workout! Beautiful views. Plenty of variety too - rolling hills and mountains and you are in wooded areas at times too! Loved this hike!

🥈 Contributor

about 3 years ago

One of the best Peninsula hikes

Starting from the parking lot on portola rd. and heading up the Spring Ridge trail via the Betsy Crowder trail to Windy Hill is such a great workout, and offers great views of the rolling hills of the preserve. Going after a rain is the best - all of the grass is green, but be careful if descending via the Hamms gulch or lost trail - they'll be muddy & slippery!

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.

about 5 years ago


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!

Nice Trail!

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

517 total saves


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We want to acknowledge and thank the past, present, and future generations of all Native Nations and Indigenous Peoples whose ancestral lands we travel, explore, and play on.

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