We plan to explore Highway 138 (waterfalls). Plan to stay in Roseburg for two days exploring the waterfalls. Then drive to Crater Lake and spend two days hiking/exploring during Mid Sept 25. Then our destination is Mt. Hood. What is recommended route with interesting stops along the way for hiking etc. One route is driving from Crater Lake to Eugene, Salem, Portland and then to Mt. Hood. The other route I see if driving from Crater Lake northward through Bend to Mt. Hood. Which is recommended and why? I value your input.

Thanks in advance for your advice.

steve

When will this be?

The route up the east side of the mountains will involve less driving and has plenty of interesting places to visit enroute. Bend itself is very nice, as is the town of Sisters. One of the highlights of the US 97/US 26/OR 35 route is Smith Rock State Park. Then, after Timberline Lodge on Mount Hood, OR 35 passes through the beautiful Hood River Valley, with its orchards, vineyards and famous "fruit loop" drive.

Map - https://maps.app.goo.gl/NBfDTHhV8jirGcrq9

Our timeline from Crater Lake to Mt. Hood is around the end of September.
Suggestions for must hikes and experiences along the way to Mt. Hood as well as Mt. Hood and Columbia River.

Agree Smith Rock is great. It is famous for rock climbing- I think you can take a lesson. There are many trails. Bill Sullivan is a hiking guru from around here. He has great books with good descriptions of the hikes and how to get there.
Bend is an active town. You could take a gondola to the top of Mt Bachelor- and hike down. There is an Urban hike in town along the Deschutes River, its easy and flat but pretty. Another hike a short distance from Bend is Benham Falls. Also along the Deschutes River. It is quite easy.
There are so many hikes its hard to pick one.
In the Columbia Gorge area I have hiked Eagle Creek which is popular. There was a big fire there a few years ago so I don't know how much it has changed.
Roseburg is in wine country - lots of wineries to try. Hillcrest Winery is a small winery with a very knowledgeable owner. Its where Pinot Noir was first started in Oregon- but there is a big tasting room in Roseburg that serves wine from many of the wineries.
No end of things to do

Edit above - it’s not Bachelor you can walk down It Willamette Pass Ski resort which is closer to Eugene. Sorry.

On our way from Crater Lake to Mt. Hood we stopped and Big Obsidian Flow off of Rt 97. Found it interesting and nice stop to stretch out legs a bit.

Try one night in Roseburg and then visit as many waterfalls as you like off Rt 138. End the day at Diamond Lake. If you can get a night at Crater lake lodge, do it. otherwise get lodging at Diamond Lake Resort.. It is 90 miles from the north entrance of Crater Lake NP to the south end of Bend.