Drive McKenzie pass and hike to Proxy falls. (pro tip: come in the early summer when the road is closed to traffic and bike it)
Also the well known brewpubs like Deschutes and 10 Barrel are good, but there can be a wait. I prefer McMenamins. Or Bend Brewing. Or... there are many options.
The usual recommendos. (Popular with good reason, but you won't find solitude or parking spots on weekends)
- Tumalo Falls and North Fork trail. Beautiful hiking up the creek beyond the main falls.
- Green lakes trail. Nice family hike. mosquitos.
- Any of the lake resorts would have fun stuff for the family (Elk Lake and Cultus are closest. Or if you drive McKenzie, loop back on 126 and you'll go past a couple more that way)
If not traveling with family I would rent a Tallboy from Pine Mountain and ride the crap out of it. (see bendtrails.org). If with kids maybe the trails near the town of Sisters.