Certainly Oregon has a well-deserved reputation as a great destination for beer lovers. And while Portland gets the lion's share of the attention, a few hours to the east, Bend has 5 excellent breweries all within a short walk of each other and a sixth is just 5 minutes away by car.
Cascade Lakes Brewing - The Lodge
Start here, as you'll have to drive a short ways downtown to walk to the rest. If the Angus MacDougal's is on tap (it's a seasonal) be sure to try it!
McMenamin's - The Old St. Francis Pub
Start the walking part of your tour here at the south end of downtown on Bond St. My suggestion is to try the "Rubinator," a 50 / 50 mix of Terminator stout and Ruby ale.
Less than a block up Bond St. on Franklin is JC's Bar and Grill where they have just started a brewing company. They're so new, their only website is a MySpace page! No worries though, the bar is smoke free and their beer is good.
A couple blocks further north on Bond you'll find the granddaddy of them all: the Deschutes Brew Pub! Try the Black Butte Porter and jalepeno cheese dip. Whatever you do, DON'T ask for Coors Light...
Bend Brewing Company
Backtrack just a little to Oregon Ave. and walk down a block to Brooks St. There you will find a less famous but also less crowded place with excellent brew.
Silver Moon Brewing
Finally, head back to Deschutes, but continue past them and out across Greenwood. Walk down that side of Greenwood about two blocks and you'll run into another newcomer on the scene. Silver Moon is a very casual place that frequently has live music. Try the Pilsner!
Dress Code: Being an active, "outdoorsy" sort of town, Bend tends to embrace the casual look. And nowhere is this more true than at the pubs. Shorts with rafting sandals are practically a uniform here in the summer. In the winter, you'll definitely want to bundle up as it can be quite cold.
Club 97 is about the only spot in Bend where people go. There is a great mix of people and music. Where what you want. It is primarily young people but there are older people there. Saturday night is the best night to go. Thursday night is comedy night and there is a comedian. I think it starts at 8pm. If you like strip clubs there are 2. One is called The Office, and the other is Stars. I've never been to the strip clubs.