Tour de Menlo - 106k route for a newbie?

I'm new to road riding, and am comfortable doing 25 mile rides 2-3x a week, on mostly flat rides with some gentle hills, averaging 14-15 mph. I saw some posters for the Tour de Menlo ride on August 16, and am wondering if I could pull off the 106k ride. The shorter, 54k route would be a piece of cake (the route is basically the reverse of the ride I typically do on Foothill), and I'd like a bit more of a challenge.

Am I crazy to even consider the 106k ride? I'm concerned about the hills and the ride length, but I feel like I could probably do it. Thoughts?

do a 65 k next weekend and an 80 k the next and you're there?

The other thing you would want to take into account (besides the distance) is the amount of climbing on the course. Both Jefferson and Montebello are probably the two most challenging on the course. It doesn't look like the route takes you to the top of Montebello but to the Picchetti Winery. But both of these climbs have fairly steep sections and for someone new to road biking could be fairly challenging. I would recommend trying to ride these climbs before hand as to get a feel for what to expect.