Deschutes River Trail in Bend for biking. Really beautiful MTB trail right along the river. Popular for hiking too. Trails in western OR are probably still too muddy to bike this time of year.
Smith rock of course is great for hiking and sight seeing.I forget the name of the place where people usually car camp near smith rock. Google and you will find the popular place where all the climbers camp.
Newberry National Volcanic Monument is like a mini crater lake sort of with a caldera lake. It's really cool and I've car camped there. (My friend swears we were visited by some sort of Squatch but it was probably just a bear).
If you are camping check the weather because sometimes it is dryer in central OR than the willamette valley or vice versa.
As for night life, well I like live music and if you search good chance there is something you'll like in either Bend or PDX since there are tons or local and traveling acts all the time.
Distilleries in Bend and PDX have fun tours tastings. Breweries all over this state, tons in bend and Portland. Wine tasting in the Willamette Valley. Willamette Valley Vineyards is a fun one check out (I own stock in that place lol)