Apparently Ollalie is closed this year per several postings on the PCT-L from several months back.
My experience from 06:
You can buy very limited supplies at the resort at the west end of Odell Lake (Shelter Cove, I think it’s called), just before Willamate Pass. I picked up some burger buns to replace the stale bagels I’d mailed from Ashland.
At this point, if you were REALLY wanted to only buy as you go, you might be able to hitch west on Hwy 58 ~30 miles to the (somewhat dumpy) town of Oakridge, which is full service (I was just there last weekend). There’s a Ray’s food place (full supply grocery), multiple hotels, some restraunts (one of which really sucks - I won’t name it but it’s on the north side of the Hwy, toward the east end of town, others which are fair to good). It’s a bit spread out, about a mile or 2 long. You should be able to find what you need. Hwy 58 has a fair amount of traffic, but it’s hard to say what hitching to and from Oakridge would be like. Oakridge caters to the MTB crowd, so there are a fair number of outdoorsy types in the area who head up into the hills and ride back down. This may help with hitching, if not all the way back to Willamatte pass, then at least close to it.
Further north, you can hitch into Sisters (or further to Bend) from either McKenzie Pass or Santiam Pass. It’s full supply at both towns. You could carry from either of these points to Cascade Locks, although it would be quite a heavy load. I really liked Sisters and highly recommend this as a town stop.
There wasn’t much to buy at Timerline - just some candy bars. Of course, depending on how much you can eat, you could pig out at the amazing AYCE breakfast buffet at Timberline then speed run to Cascade Locks
(not a serious suggestion, of course).
If you mailed supplies to yourself, you have Shelter Cove, Elk Lake Resort, the youth camp between McKenzie and Santiam and of course Timberline to choose from.
Token Civilian