Dear Scootsmoon.
In my vast experience in Oregon I have found that it is best not to eat east of the mountains. I spent my first 18 years in Pilot Rock and Hermiston. I visit often. I live on chicarones and beef jerky.
I do remember a few hotspots. The fry bread at Kahneeta is good. Eat it and soak in the hot water.
it's good. If they smoke some salmon, that is great.
The berry pies are good everywhere, as is the Mexican food. Mexican is the roadfood of Eastern Oregon. There are lots of small, family run places that serve their own favorites from south of the border.
There is TexMex, but there is also a surprising and varied amount of vegetable based sauces. My favorite is a green mole made from pipian. I like papusas, a very thick tortilla like thing with cheese
and lorocos, which is actually Salvadorian. Ask about their specialties, ask them what they like. Ask where their family comes from.
Your best bet is to get invited to somebody's house. I have eaten great Basque at people's houses: beef roasted in red wine sauce, zucchini and onion, great bread.
I've had turkey mole to die for. There is a bed and breakfast near Pendleton that sounds for all the world like a dinner at my aunt's DeSpain Gulch ranch.
Mr Chips and I often go to the Oasis on Stateline Road near Milton Freewater. It's a steak house. it It has a variety of good food and lots of atmosphere. Ask them for directions to Helix, which has a great pie house.
I stop in Mosier for pie or anything made with berries, and sandwiches.
Hood River has great fruit stands and a few good restaurants. I heard that the Columbia Gorge Hotel is open again. I hope they are still making their biscuit and honey breakfasts. If you get there let me know.
In Bend, you can go to my favorite McMenamin's. Francis School? St Francis School? They have a variety of good burgers and beer. I like their clam chowder.
If you get bored invite Mr Chips and I to join you somewhere. trudyn