Windy Hill Open Space Preserve - Hiking Day Trip

NO SHOW is unacceptable for respecting others and yourself. If you cannot make it to this hiking event, please kindly change your RSVP to "NO." Please don't just show up without RSVP! Thanks for following the policy!

In brief:7.2 mile loop starts in Portola Valley and climbs to the crest of the Santa Cruz Mountains, then drops sharply back through grassland. Very pretty and cool in summer fog.

What to bring: Water 2 liter bottle, Lunch, Sun protection gears/sunscreen, Dress in layer with hiking gears, a backpack.

Distance, category, and difficulty:This 7.2 mile loop hike is moderate, with about 1400 feet in elevation change. There are two main trailheads: the Portola Valley Trailhead elevation is under 600 feet. The Skyline Boulevard Trailhead elevation is about 1800 feet. From either trailhead, you can create easy or moderate hikes on mostly level trails, but as soon as you start climbing or descending, the hiking is more challenging.

***Start at the information signboard. Walk west on a flat path >Turn left (toward Alpine Road) >Turn right Meadow Trail>turn left onto on Hamms Gulch Trail>Turn right on Lost Trail>Anniversary Trail>Turn right on Spring Ridge Trail>Turn left on Betsy Crowder Trail>Turn left and retrace your steps to the trailhead***

Exposure:The climb to the ridge is mostly shaded and the descent is mostly exposed.

Trail traffic:Moderate.

Trail surfaces:Dirt trails and fire roads.

Hiking time:3-4 hours.

Season:Nice any time, but best in early spring.

Getting there:

From Interstate 280 in San Mateo County, exit Alpine Road (exit 22). Drive west about 3 miles, and turn right at the first stop sign, onto Portola. Drive about 0.8 mile, and turn left into the parking lot.

Trailhead detail















Large parking lot. No entrance or parking fees. Maps available at the information signboard. No drinking water.

Map: http://www.openspace.org/preserves/maps/pr_windy_hill.pdf

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  • A former member
    A former member

    scenic hike suggestions...
    Tin House via Tanbark trail at Julia Pfeiffer State Park at Big Sur - see condor and crashing waves below - tougher hike than Windy Hill but doable to all. 2hour drive south but we can plan late lunch at Monterey or Carmel.
    Pinnacles state park - incredibly beautiful rock formation from top (feel that Moses & God is around the corner). Very tough but doable if we go slow with a lot of rest. 1.5hr south.

    ... beautiful Chinese NY Parade finale last night - anyone see it? Miss the smell of firecrackers!

    1 · February 16, 2014

  • Yvonne C.

    Windy Hill just like its name, so windy! I notices our hair all messed up by the strong wind except those wearing hats. ;P However, it's really a scenic hike, it's worthy to have my hair all messed up by the end of the hike with my fun hiking group. Thanks God for a happy day!

    February 15, 2014

  • A former member
    A former member

    fun hike

    February 15, 2014

  • Jingmei

    From 280 in San Mateo county exit alpine rd exit 22, drive west about 3 miles, turn right at the 1st stop sign, onto portola, drive about 0.8 mile, then turn left into the parking lot.

    February 15, 2014

  • A former member
    A former member

    Last minute changed of work schedule

    February 14, 2014

  • Sai C.

    Alright time to hike again!!!!!

    1 · February 14, 2014

    • Yvonne C.

      glad you recover from your cold!

      February 14, 2014

    • Sai C.

      Still have little bit but little exercise would not hurt

      February 14, 2014

  • Yvonne C.

    It may rain tomorrow, but I think just a little shower, so you should dress in water resistant clothing. :)

    February 14, 2014

  • Feng Y.

    Cannot make it this time, sorry for short notice.

    February 14, 2014

  • Gracie

    Coming from Sunnyvale and need carpool ride. Please private message me for details...contact number, location and time of meeting.

    February 12, 2014

    • A former member
      A former member

      glad to give you a ride - can you meet at Lucky parking lot next to PAMF at El Camino Real & hwy85? Or if you don't drive let me know & I'll pick you up as I am next door to Sunnyvale

      February 13, 2014

  • Yvonne C.

    The RSVP is opened again if you are interested, you can get on the waiting list 1st....

    February 13, 2014

  • Tree

    I injured my knee while skiing. I am going to have to give up my spot. Who will be the lucky one that can join Yvonne's popular hike?

    February 10, 2014

    • Yvonne C.

      sorry to hear this, take good rest, see you the next hike.

      February 11, 2014

  • Yvonne C.

    If you would like to meet at 99 Ranch Market in Milpitas Square for carpool, please post your comment. Otherwise, you will need to arrangement your own carpool. Please kindly share gas expense with your driver. Suggesting $20 per car due to the distance, splits with other passengers (bring cash your own). It's about 40 minus drive from Milpitas to the park, Carpool will meet at 9:30am in front of 99 Ranch Market. Thanks! :)

    February 10, 2014

    • A former member
      A former member

      Yes for carpool

      February 11, 2014

    • Richard

      I'll meet you guys for carpool.

      February 11, 2014

  • Yvonne C.

    If you are new to my hiking event, welcome to my Feb hiking group. For the 24 RSVP hikers, I will see you all this Sat, hopefully it will be a nice day without rain during day time. In case, you needs to reach me by phone @[masked], please only call on 2/15 sat if you get lost. We will meet at the parking lot @ 10:30am from Portola Rd.

    February 10, 2014

  • Will M.

    哇哇哇哇aaaaaaat? Sign up almost one month early and still waitlisted. I miss you guys!

    1 · January 21, 2014

    • Yvonne C.

      Lol...thank you! ; )

      1 · January 23, 2014

    • A former member
      A former member

      like Will's digital calligraphy skills

      February 5, 2014

  • A former member
    A former member

    Dinosaur (old) new to the group & hoping to learn some Mandarin (don't know any Chinese). Coming from Mtn View PAMF @hwy85 & El Camino & can give rides.

    February 5, 2014

  • Yvonne C.

    This is not an easy hike, make sure you read the detail!

    January 21, 2014

  • Christina

    Can I bring couple friends to hike with or do they have to sign up before they can hike with the group?

    January 21, 2014

    • Yvonne C.

      Yes, due to the popularity of my event, your friends need to RSVP as well. Thanks!

      January 21, 2014

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