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Not a route I have much experience with, but I think I'd find my way to 35 and ride that until Cañada, then finish out the Woodside loop in the CW direction and come back Foothill to Fremont. Not sure how it looks at night, but it's a very popular day time route.
 

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Does Stanford have good ER trauma centers?

Seriously, don't do it.
 

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I recently rode up to Mill Valley and back for a ride (spent the night up there).
This is the route I took up there from San Jose.
https://www.strava.com/routes/4966998

So when I mapped out my way back, I pretty much did the same thing back from Mill Valley to San Jose (goes near Sunnyvale).
https://www.strava.com/routes/4994388

I would take the route again. The only part that was sketchy was Skyline near the overpasses. Really, Skyline in general feels a little like riding on a freeway and is boring as heck but it has wide shoulders so it could be worse, I never felt in danger for my life or anything (your mileage may vary).
 

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I agree with earlier comment that 35 would be the way to go, though it is not a great route (the lesser evil). I have ridden other routes to mid-Peninsula and they get complicated and have lots of cars. 35 is most direct and bike friendly, but also has more climbing than other routes.

For any route, it would be good to have a smartphone on your handlebars with Google maps running directing you with a bike route.

Basic daytime route (* mark changes for night, ? marks something I am not sure about - detailed below):

favorite route to Great Highway
Great Highway ??
35
San Andreas Trail *
Cross to other side of 280 at Larkspur to take Skyline Blvd for 1 exit
Cross back under 280 at Hillcrest to Sawyer Camp Trail **
Sawyer Camp trail to Skyline
Skyline to 92 ???
92 to Canada
Favorite route home from there

* - San Andreas trail closed at night - if you get there after closure, you have to ride shoulder of 280 for 1 exit. It is legal.
** - Sawyer Camp closed at night. If you get there after dark, you ride 280 for 1 exit south (Truosdale) from north end of trail. Exit, cross under 280, then right on Skyline. Right on Hayne Rd and go back under 280. Left on Skyline.

?? south end of Great Highway has been closed to cars for a while, but I think it is still open to bikes.
??? - the big question that I don't know is the status of Skyline near south end of Sawyer Camp and above dam. Last time I drove past the area, it was closed to motor vehicles. Not sure if it is open to bikes or not.
 
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