Chilly Hilly: 33mi, 2675' (I rode to/from the ride for a total of 81mi, 4950')
Chelan Century Challenge: 100mi, 9300'
7 Hills of Kirkland: metric century, 4600' (might do the full century, 7000', but I'm riding the TdC century the weekend before it.)

My new found addiction is hills. I've got around 1600' daily in my 22mi r/t commute, and I keep looking for steeper and longer hills to ride. I'm building my way up to riding the High Pass Challenge (114mi, 7000+ elevation gain, 10hr time limit) and RAMROD (150mi, 11K elevation gain)
I'm not so concerned with the weather being good or bad, except that I don't like riding long distance in really cold, wet weather. Just make sure the course hasn't got too many dead-level roads.