There is no excuse for visiting Portland without drinking a lot of excellent beer. BridgePort Brewing, Rogue Ales, Deschutes, Full Sail, and Cascade are all in town and every local will be more than happy to explain which one they think is best. For a foodie treat, hit the bars on the east side of the Willamette River, but spend evenings in Old Town, where the line between strip clubs and normal bars has gotten extremely blurry and local guides seem to be smoking next to every taco truck. Voodoo Donuts may be the epicenter of the madness, but a fruit loop-encrusted pastry is not the strangest thing you're likely to see.
More information: JetBlue flies to Portland direct from New York's JFK International. Groomsmen coming from the east coast shoot try to book a seat on an Alaska Airlines flight. It's not an original choice, but the Ace Hotel is hard to beat.