I also realize time of year is important, I’m thinking of doing this trip within the next few weeks, or next fall.

I’m going to be wanting to do some fishing, and lots of sightseeing.

Water… good point… the first 145 miles there are quite a few fresh water sources… the last 100 miles not so many, but the last half has a lot more shopping opportunities and would be mostly down hill.
Food… for backpacking I normally eat lots of trail mix, granola, jerky, oatmeal, dehydrated fruits, you know trail snacks. For dinner I might splurge and make a one pot hot meal. I was figuring on packing enough food for 24 hours and resupply as I come into small towns (also resupply water stops). Again the second half the trip is a lot more opportunities to shop or eat at a cafe.

The first campground is only 22 miles away, and is at the base of the steep incline. From there until mile 200 I can camp just about anywhere. So by the sounds of it, I should plan a 3 to 4 day trip to be able to include side adventures, fishing, and maybe a day of just relaxing.