Cycling around Cupertino?

Is anyone on the forum from the Cupertino area that can share some good road cycling routes? Looking for rides less than 40-miles due to time constraints. Obviously I’ve looked at Strava and RideWithGPS, but hoping to get some firsthand local knowledge of which are the best places to ride.

Drive up 280 to Palo Alto / Woodside and climb Old La Honda. There are some other, closer, climbs up to Skyline, but I haven’t lived on the Peninsula in decades.

see: Cycling around Cupertino? - #7 by RJones07

An old friend lives in Menlo Park near Facebook headquarters. A few rides from his feed…

Plenty of options available. Check out this loop:
Portola Valley Loop | 22.7 mi Cycling Route on Strava
Rid to this from where ever you are and you can do it in either direction. If you have time, you should do it both ways. If you want to extend the ride, you just go further north at Canada Road which is at the intersection of Woodside Rd (hwy 84). There’s Robert’s Market there were you can fill water. Also, water is availabe outside of Robert’s Market, at the intersection of Alpine Rd. and Portola Valley Road in a little park area next to the dirt path. Good luck and have fun!

Unfortunately I won’t have a car, other than taking Ubers which means traveling with my bike will be too cumbersome. Just looking for rides starting in Cupertino.

From Cupertino with no car, I’d check out an out-and-back on Steven’s Canyon (which I always called Cupertucky… I’ve been stopped by chickens running around here), the Mt Eden / Pierce loop, or an out-and-back on Montebello Rd. I haven’t lived in the area in a few years but these are all pretty classic and I assume they’re in okay condition. If you enjoy causing yourself physical pain you can ride up Redwood Gulch.


Not a great idea on a weekend right now with Hwy 84 still closed. Lots of traffic is diverted to either OLH or Kings, and most of those people don’t know how to drive mountain roads, let alone with cyclists. I’d suggest Stevens Canyon + Redwood Gulch as above and you can continue up Hwy 9 to Skyline depending on how much time you’ve got and if you want to do some climbing.

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As a local I second Steven’s Canyon to Eden & Pierce, then down 9 to Saratoga and back to Cupertino. Redwood Gulch (and the end of Steven’s Canyon) can be a selection depending on how much pain you’re willing to inflick on yourself. Same goes for Montebello, where the first mile and a half can be very tough, but things get easier once you get over that first stretch. Montebello also has a mix of exposed and shaded sections, so that’s a plus. Also has great views too.

I would jump on to Foothill Expressway and head north. For a shorter loop and climb, I would head up to Moody or Altamont Rd via El Monte. You can continue up to Hwy 35 via Page Mill. It’s been awhile but my recollection is that most of the traffic dies down after Foothill Nature Preserve. I normal skip the lower section of Page Mill. Too many idiots driving & blocking the descent. For slightly longer ride, head up to Arastradero Rd for the Alpine loop (Alpine, Portola, Sandhill to Junipero Serra). If you want to add climbs, I like Old La Honda and down Hwy 84. To add more miles, you can head up to 280/92 interchange via Canada Rd.

You can always head up to Stevens Creek Reservoir. Not sure how busy it’s these days. I would stay clear of Hwy 9.

IMHO, Stanford and Portola Valley is much more cyclist friendly than elsewhere of the peninsula.

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Cupertino to San Jose to climb Quimby Road, descend Mt. Hamilton, go up Sierra Rd. Will be a fun climb.

Cupertino to San Jose to Hicks Rd and up Mt. Umunhum is also a nice one

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Thank you everyone for the recommendations! The climb up and around Steven’s Canyon/Montebello/Eden look great.

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Are any of the bigger streets/roads within the city (Stevens Creek, De Anza, Lawrence Expy) too crazy to ride on? I’m in L.A., so riding with cars I’m used to, but don’t want to be on a high speed highway with no lane or space for me to ride along.

Of you ride in LA traffic this will be very chill.

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I think your best bet here would be to look at the biking layer on Google Maps for Cupertino and plot out your routes with that. I think Stevens Creek and De Anza both have bike lanes but I shuddered when you mentioned Lawrence Expressway.

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Stevens Creek & De Anza Blvd between the Hwy 85 & i280 are basically express ways. I would stay clear of them.

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Concur. Alternate routes exist.

Thank you to everyone who provided recommendations. I ended up riding a few days during my work trip around various areas of Cupertino and Sunnyvale like around Baylands Park the trail through Levi Stadium. I capped it off before my flight home by riding up and around Montebello Rd, including the gravel sections then descended down Page Mill and back on the Foothill Expressway. The roads were completely empty early on Saturday morning and so that was very enjoyable.