I've also lived in San Jose for 7 years, and Denver...

...the weather is better in Denver. Because it has seasons.

But worry not, winter does not relegate one to trainers. Because the snow rarely "sticks". You could very well in December have a beautiful sunny 70*F in the morning, a strong snow dump overnight, and have it melt the next day with T-shirt temperature.

The hills start west. Usually I roll from the REI downtown or to cut the warm up mileage just drive to ken Caryl or something with the car