If you’re looking for something to do tonight to kick off the weekend, don’t forget tonight is First Friday in Downtown Bend and the Old Mill District: when art galleries and other downtown businesses open their doors late for special receptions and art exhibits, and many have live music and free refreshments and wine as well. The overall events run from 5 to 9pm.
The Downtown Bend site has a good list of participating businesses, and in addition to that you might want to check out The Wine Shop: they are hosting a beer tasting featuring New Belgium Brewing, with pint specials and giveaways in addition to the tasting (which will run from 5:30 to 10:30).
Also, you can catch the free GETIT shuttle driven to take you back and forth from downtown Bend to the Old Mill District. The shuttle runs from 5 to 9:30 and leaves from 900 Wall St. beginning at 5. The loop is about an hour and is free for riders.