Glad you are visiting Oregon! The route between Mill City and Bend is fairly remote and mountainous. There aren’t a whole lot of towns in between – but two spring to mind that you could check out. Sisters is just 30 minutes from Bend. It’s a charming western-themed town with some good shopping and restaurants. Try the Lakeside Bistro at Black Butte Ranch (actually 10 miles west of Sisters), Angeline’s Bakery, Los Agaves Mexican Grill, or Cottonwood Cafe for a meal here. The other small town you’ll pass through, on the other side of the mountain summit, is Detroit, on a lake and in the mountains. It’s smaller than Sisters – try dining at the Korner Post. Up the road from Detroit is Breitenbush Hot Springs. You can stop in for a day visit at this lodge and retreat to soak in the warm waters. 

Have a great trip!