https://i.imgur.com/BxDJC6f.jpg (direct link)
https://imgur.com/a/FiEGm (Imgur page in case the above doesn't work)
The map appears to date from the early 1970s: Highway 280 is there but appears to have Cañada Road routing from before the ridge freeway was finished. Or I could be misreading that part of the map and it is from later, maybe the 1980s?
It's interesting how many inaccuracies there are. Living in Menlo Park, I checked a few local landmarks. Palo Alto Airport is in the right place, but where is San Carlos Airport? They seem to have moved it across the street from Facebook!
And note the airport near where 280 and Highway 92 cross.
The map is also very hard to read. Look at Highway 101. Unlike 280, it's mostly in white, but if you follow it through Redwood City just north of Woodside Road (Highway 84), it looks like 101 is routed along Veterans Boulevard - which was bypassed years before this map was made. If you look again, there is a brown stretch that is close to the actual freeway alignment.
Then follow 280 down into Los Altos, where it changes from brown to white as it approaches Cupertino and into San Jose. This bit of randomly swapping freeway colors between brown and white seems to be a common theme.
Many of the local streets are recognizable but have a very approximate hand-drawn look to them. I'll be curious to hear what anyone else notices in their neighborhood.
This is easily the most interesting, and worst quality, map of the Bay Area I've seen. I wonder why it has so many little things wrong, when they could have simply sent a spy into any local gas station to buy an accurate, well drawn, and easy to read road map?