Smith Rock has climbing for everyone from 5.7 and up :) There are also some hiking trails that lead you to nice views. It's worth checking out if you have the gear and the time.
Tumalo Falls is a striking waterfall located right outside of town. You can hike up to it and further down the trail to see several additional waterfalls, or you can park and see it right from your car, making it accessible so those who like to hike and those who prefer not, both!
The Old Mill District is an outdoor Mall if you want to do some shopping. It has a lot of the classic mall stores, but I like Vanilla Urban Threads. There is a movie theater here as well, and Charlie and I like to eat at Hola!
This is the home town hero of the local breweries, because they refused to sell out to Budweiser (unlike 10Barrel, which is also good). They have a spot right downtown and tasting room with a tour located at: 901 SW Simpson Ave, Bend, OR 97702. The tour costs $5. You get a beer and free tastings. The downtown location has good food too! Just a friendly reminder that there are 35 (maybe more) breweries to check out in Bend!