The Western Spine of Silicon Valley: Black Mountain (Montebello Open Space) to Alice’s Restaurant


From down in Silicon Valley, the Santa Cruz Mountains separate the valley from the Pacific Ocean. From a distance it can look ominous. Up close you’ll see homes, a rock quarry, a few wineries, and some towers on Black Mountain if line of sight allows you to see beyond some smaller hills.

As you drive from I-280 and pass the Steven’s Creek Reservoir and the quarry, you’ll then see a right turn onto Montebello Road. Montebello Road goes up about 6 miles, past a few wineries, an old elementary school, and on to some magnificent views, but..there’s NO PARKING anywhere up there…unless you know who to ask!

What to do? Bicycling from the reservoir is possible. I’ve done it a few times in a very steep 80 minutes. I have also asked Ridge Vineyards ( if it was possible to park there and take a hike. They seemed OK with it if you were there for the winery also. Unfortunately, they’re only open weekends!

The “little secret” to easily access the trails up here is to apply for a permit for “Permit Parking Only” at the Waterwheel Creek parking lot. Fill out the form a day or two in advance, and you’ll get a printable permit by e-mail and the combination to the gate! You can park all day, during daylight hours, very close to the top.


My goal today was to head north, either paralleling Skyline Boulevard on safe trails, or cautiously riding on the road itself. The road has little or no shoulder, but there are quite a few cyclists up there and not much weekday traffic.

I left my car behind the locked gate at 9:00AM, and was soon headed up the remaining grade to the summit of Black Mountain. (The coast is out there, under a fog bank, about 20 miles away)


From there, it was mostly downhill or flat cycling to Page Mill Road (which is has a public parking lot), then up the road to Skyline Blvd. I decided to “go for it” on Skyline to go as far as Alice’s Restaurant

On the way I passed the Thomas Fogarty winery, with it’s attractive sign and vineyards visible beyond.


About a mile before arriving at Alice’s, there’s a steep and winding stretch of road where Joy Covey tragically died recently. She was the first CFO of Amazon, as well as playing other valuable roles in the early days of the company. An OnTrac truck (ironically delivering packages for Amazon!) turned left across her path as she was coming down the long downhill section. There were bunches of flowers at the base of the street sign. She left behind an 8 year old son.


Onwards to lunch at Alice’s, and back the way I came!

– A beautiful autumn day
– A “secret” parking area
– A great bike ride
– A solemn visit to a fatal crash scene
– Lunch at Alice’s

Oh yeah..then there was this guy on a tree crew in Portola Valley who was carving a bear on his lunch hour! I’ve only seen this done up in the Sierra for the tourists.


More Photos:

GPS Track:

About AlphaRoaming

Random outdoor roaming: hiking, cycling, camping, backpacking & plotting more of the above Grew up on the edges of the Adirondack mountains of New York, just a bit west of Vermont. Now living in Silicon Valley and venturing out when and where I can!
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