I would suggest using Hood River as a base for your two days here. Lots of lodging options, brew pubs, wineries and it’s right on the Columbia River. It’s also a great spot for easy access to the recreation areas of Mount Hood and the Gorge. Mount Hood Adventure is a great company to contact for help with planning horseback riding and other adventure activities.
Downtown Troutdale has a few good restaurants, art galleries, and antique shops. The real attraction in Troutdale is McMenamin’s Edgefield. Several restaurants, glass blowers, bars, and the winery. It’s a destination in itself. It was once a poor farm, and they have restored it to a hotel, along with the other things I previously mentioned. You could easily spend a few hours just wandering from bar to bar and touring the grounds.