Take Part in the Beer Scene
Oktoberfest can happen any time of year around these parts. Although the number could be higher or lower on any given day (and that doesn't include tiny garage growler experiments), there are currently 22 breweries within the city limits and 28 in nearby towns of Central Oregon (three in Redmond, one in Sisters, one in Prineville, and one in Sunriver). Sixteen that have tasting rooms or restaurants with regular hours have banded together as the Bend Ale Trail.
If you have the liquid courage, try the challenge. Pick up a passport booklet at the Bend Visitor Center and collect stamps as you visit the suds slingers such as 10 Barrel, Bend Brewing Company, and Crux Fermentation Project. Collect 10, get a prize. Collect all 16, the B.D.V. will give you an extra prize, and if you hit them all during Bend Ale Trail Month (AKA November), you will even get a trophy.
Deschutes Brewery, which opened in the late 1980s and is one of the founding fathers of fermentation in the area, has four free tours of their production facility daily. You can also visit a hop farm. Many double as restaurants or have outside areas with live music, lawn games, food trucks, and more, making them kid and dog-friendly. Seasonally-inspired and sour beers are all the rage.
If you are "meh" about malted grains, there are a growing number of Central Oregon distilleries, cideries, and wineries to lift your spirits including Atlas Cider, Cascade Alchemy (which makes chai tea vodka and apple pie liquor), Backdrop Distilling, or Faith, Hope And Charity Vineyards. To help everyone drink responsibly, the free Ride Bend shuttle runs every 15 minutes from 2 p.m. to 10 p.m. during the summer. The Bend Brew Bus has beer-centric tours as well as a combo tour called The Local Pour.
If you prefer your pale ale with a side of pot, good news! Recreational marijuana is legal in the state for people 21 and older, but visit whatslegaloregon.com to determine where you can get lit before you light up.