To the OP, when you talk about rides, are you looking at out-and-back stuff, meaning a 60 or so mile loop from where you start, or are you going to do any touring/camping?

If you wanted to go to Bend, a good out-and-back would be heading up to McKenzie Pass. Quite the climb, yes, but a beautiful/weird landscape at the top, and a great descent back down. And Sisters, a small touristy town you'll pass through, has Three Creeks Brewing. And of course Deschutes is in Bend.