I'll strongly second the Cole Creek recommendation. There's some pretty good, down the fall line terrain off Grizzly Peak as well, but Cole gets you much more vertical per run and a faster turnaround, with a lot of terrain to explore (don't miss Headwaters).
Drainage is definitely fun terrain, but I don't know that I've ever made it through there without hitting something. I'd try to get at least one run down to Palisades and a run through one of the Mines on your agenda, although Palisades is probably best explored after getting a good filling of Cole Creek.
Foster and Logan's was my personal preference for a bison burger and draft cider; Natali's Front Bar is the grown up room for Red Lodge Pizza Co (shared kitchen and menu, solid pizza and a decent range of other options) and a pretty good spot to hang out and chat. Snow Creek can get rowdy and may or may not be compatible with early morning plans. The Blue is a classic dive and, last I was there, was cash only (but they have an ATM on site).