Bike planning

I've been sort of saying I want to do more "real" bike rides this year (especially after failing to do any organized rides at all last year). I think "do all three CRW centuries" is a bit of a pipe dream, but what actually is when?

• CRW Spring Century, May 17. Looks like it's about a unit inland from the GSW Seacoast Century. I almost certainly can't do a full century then (both one and three weekends before I'm out of town) but the half or metric centuries could be interesting.
• CRW Climb to the Clouds, July 19. Will I actually do it this year? The hard part would be preparing myself for Mile Hill Road, the distance itself is probably doable (especially if I do ramp up to 60 miles by two months before).
• CRW Fall Century, September 20. I've eyed this before and it looks like it heads for the "northwest from Fitchburg" corridor, but never actually tried it. Reviews from before worked out to "somewhat scenic, rural, definitely easier than CTTC".
• GSW Seacoast Century, September 26 or 27. This is the one I've actually done. Easy terrain, but miles 70-90 can run into a terrible headwind.

In theory nothing stops me from doing all of these. Matching it up with the bridge schedule could be exciting. It's already reasonably bikeable now, though (my bike computer already has about 50 miles for the season) and if I'm serious about ramping up I really could do this. But, it also means being reasonably serious about my weekend biking, and probably a little more planning my weekends around it and going out even in not-perfect weather.