Won't be doing the race (cat 5), but did ride up Wachusett a couple weeks ago....
I was a bit disappointed, probably due to inaccurate expectations....Lived in the SF Bay Area for many years and had my own preconceived notion of what a climb to a 2000ft summit should be....long steady climb going from more or less sea-level to 2000 ft....Been living here now for about 6 years, and jsut getting back to cycling so figured Wachusett would be the closest opportunity for the climbing I used to love...instead found a series of short steep sections interspersed with much flatter if not downhill bits.....The ride back and forth through Worcester didn't help much either.
That said, the Princeton area was awesome for riding....maybe I'll be a 4 next year and give it a go...