I've always liked the hwy 20 Santiam Pass to Bend. Takes you through some of the prettier parts of the cascade range.

I can recommend some good food in the Hood River area

In Hood river
Breakfast/Lunch, home cookin':
Betty's
Egg River Cafe

Lunch/dinner:
Full Sail Brewery (best beer food ever)
Mesquitery (awesome steak, pasta)
Double Mountain Brewery

In Bingen/White Salmon (across the river)
Lunch/Dinner:
Killer Burger (one of their burgers requires a waiver, it's so spicy)
Solstace Cafe (won a taste test for best pizza in WA)
Henny's (a bit fancier)
Everybody's Brewery
Los Reyes (Mexican food, tasty)