microbrews - bridgeport, any of the mcmenamin
hike at the gorge - angel's rest, wakeena fall
eat at apizza scholl, pok pok
Speaking of buffalo wings, for a so-so but still tasty/fun experience (lots of sauces to choose from!) hittup fire on the mountain. Two locations so it's easy to get to.
Watch out for the gorge hikes mentioned - don't bother if it's a weekend and not raining - the amount of people on the trails is unenjoyable. Swing a weekday to avoid the crowds, or hike when it's rainy (still cool, but I am an oregonian...)
$11 for the plate of wings is actually not bad. It is pretty big. And they are really delicious. If you get cocktails and go all out it is gets expensive. No doubt. The cocktails are killer too
Regarding the gorge: some hikes are fine on weekends. Eagle Creek Falls trail requires a $5 per car day use fee, which keeps out the crowds. It's one of the best trails in the gorge. Skip it if you don't like heights though, and be careful if it's raining.
I'll have to checkout the whiskey lounge, and great tip on Eagle Creek. Gotta love that slick drop off to the raging river below :)