For those coming to town around Labor Day looking for rides (or locals who would like to meet up as well of course), I'm going to do the following -

Friday Aug 30 - Lower Phil's > Upper Phil's > Helipad > Whoops > Bens
This is a (arguably the) classic Bend ride. Upper Phil's is rated as Difficult, but mostly because of a few walkable rock sections. Whoops is DH/Gravity oriented but can be done on any type of bike. Recommended after-ride spot is 10 Barrel.

Saturday Aug 31 - Peterson Ridge Loop
Peterson Ridge is never crowded and has one of the best and most convenient after-ride spots, Three Creeks Brewery in Sisters, which is literally ride-in, ride-out.
Peterson Ridge is intermediate XC, mostly for rocks. There are several great viewpoints as well.

Three Creeks Brewing | Sisters, OR

Both rides are about 2 hours. If we start around 2PM, that puts you at the brewpubs just in time for happy hour. Please respond to this thread or PM if you're interested or have other ideas.