If you are going to go the Deschutes area and have an extra day or so you should go float the upper John Day. Mid Sept. is a great time to go. Give the young guys at the Riffle Fly Shop in Madras a call they fish and hunt in both areas. The Hazels are good but charge $500 a day (that is not a typo it says $500) for a guided steelhead trip. Both shops have a website.
In the Maupin to Macks Canyon stretch, you can fish a floating line from the time the fish first show up, around the 2nd to 3rd week in August, until mid-November. The fish are obviously freshest early, but the weather is uncertain. It can be HOT !!! The weather, not the fishing. If the weather is not hot, the fishing can be. After Labor day the weather can be a bit more reliable.
Starting about mid-October the crowds start to thin out just a bit, or maybe they just move upstream with the main push of fish. In many years, if the D runs cooler than the Columbia, some big Idaho fish will enter the D and could end up 30 miles upstream, but most will be in the lower reaches. October is a likely time for those encounters.
If you haven't been to the D, it is a spectacular desert canyon. Watch for bighorns, as well as lots of smaller critters. If you're going to do some trout fishing too, don't be misled by the size of the river. Depending on the run, the steelhead can be out a ways, but the best redsides fishing is close to shore. Sometimes you need to think inches instead of feet.
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