Take 126 east out of Eugene/Springfield to Belknap Springs.
http://www.belknaphotsprings.com/reservations.html
Continue over 242 over the McKenzie Pass to get into Sisters.
I love the hot spring experience.
Since you can't get reservation at Crater Lake Lodge, the next best choice is a motel type room or cabin at Diamond Lake Resort.
Hope that you don't hit Sisters during the annual Quilt show.
You should also check at Suttle Lake if you can't find anything at Camp Sherman or Black Butte Resort.

I would not do an overnight between Ashland and Portland. Instead, take a couple hours and stop at Silver Falls State Park, which is east of Salem a bit (20 minutes or so). There is the trail of 10 falls, which is 7 miles long and a great hike. Not hard at all. If you don't want to do the entire thing, you can park at a couple different spots and see the big falls. It would break up the day nicely.

For a night after Portland, consider the gorge. Hood River would be a good area to stay for the night. It's only an hour or so from Portland, and on the way you can take the old scenic highway and stop at Portland Woman's Forum (odd name, great views), Crown Point Vista House and Multnomah Falls. Those are the biggies, but there are many more great places to stop along here as well as for hiking. Timberline is nice too, and yes, there is great hiking right there by the lodge. It all just depends on how far you want to go and how difficult you want it.

Another place at Crater Lake is the Mazama Motor Inn. I haven't stayed there, but a friend has. It is basic, but works. Also, call the lodge at Crater Lake daily as there are always cancellations and you might luck out.

We love Timberline and there is plenty of hiking there, and the very cute lake below it - Trillium - is also beautiful.

If you want to see covered bridges - the area around where you are staying has them (Grants Pass, Eagle Point) and a bit further up - north of 5 - Canyonville and Myrtle Creek - south of Roseburg has quite a number. see: http://www.southernoregon.com/bridges/

If you also wanted to see a beautiful stretch of the Oregon Coast - at Eugene - you could head over to Florence (an hour or so) and then go north from there. This place by Depot Bay is very pretty - http://www.surfriderresort.com/

The next day - you could cut over from say Lincoln City back toward Salem and up/on into Portland, or continue up the Coast a bit further and head over to Portland from Tilamook.

Great cheese in Tilamook and a big WWII Blimp hangar that now houses an air museum. http://www.tillamookair.com/

It's a bit more driving that way - but you would see a prime section of the beautiful Oregon coast if you have not done so.

http://www.lakecreeklodge.com/

Lake Creek Lodge in the Metolius has a restaurant open for breakfast and dinner- but sounds like you have your plans made already. There is another nice restaurant in the Metolius area called the Kokanee- reservations needed in the summer.

I like MMS idea of stopping near Salem and hiking Silver Falls State park- it is beautiful hike. Some of the falls have a trail that goes behind the falls.

Crater Lake- check out lodging at Diamond Lake ( a short drive) or Steamboat Inn- also a short drive but I think kind of pricey.

I have stayed several times at the Prospect Inn-also outside the park, old stage coach stop- there is an inn part and then more of motel accommodations behind- they serve a fabulous breakfast and dinner. Its a short drive into the park and I belong to a group that stays there every winter when we do a snowshoe trip to Crater Lake.

Hiking in the Sisters area is endless- you could do a nice flat trail along the Metolius, you could hike Iron Mountain where the 2nd week of July you will find hundreds of wild flowers, you could hike Canyon Creek Meadows, Tam McArthur Rim - or drive over to Redmond and check out Smith Rock, world famous for rock climbing but there are hiking trails along the river and also more challenging ones. Fun to watch the climbers and wonder whatever possess them to want to do that.

Looking for covered bridges? Lane County where Eugene is located has the most- but Cottage Grove is the city that makes them their claim to fame. The bridges are not exactly in town- you would have to drive out in the country to find them .

Enjoy-

Have an extra cup of stumptown for me. and right down the street is voodoo donuts.

And you could do a food cart tour of Portland or a Epicurian Walking tour- haven't done the food cart tour but sounds fun.

You've already received some great suggestions for completing your Oregon itinerary, so you really can't go wrong with whatever you decide to do. I'm glad to see you plan to spend 2 nights at the Five Pine Lodge in Sisters. It's such a special property with access to endless hiking trails http://www.sistersoregonguide.com/recreation-hiking.html. As another poster mentioned, if you have time while you are in the area, take a short drive to Suttle Lake, 15 miles west of Sisters. http://thelodgeatsuttlelake.com . Getting out on the Lake in a canoe or kayak is a great way to spend a warm July afternoon. You can also dine lakeside at the Boathouse Restaurant. There's also Black Butte Ranch, 8 miles west of Sisters. You don't have to be a guest to enjoy wine and appetizers or a meal on the deck at the Ranch's Aspen Lounge from where you have a 270 degree view of the Central Oregon Cascades. http://www.blackbutteranch.com/ Lastly, for lodging near Crater Lake, there's Union Creek Resort, just 23 miles south of Crater Lake. http://www.unioncreekoregon.com/crater_lake.htm Happy Oregon Travels!

Just so that visitors to Oregon know (and my Oregon friends):
OR Rt. 58 is closed Monday-Thursday 8PM to 6AM in the area of the Salt Creek Falls tunnel near MP 56. At all other times expect 20 minute delays. This project will last through most of the summer.
The highway is open over the Willamette Pass so that you can get to Waldo Lake. I don't know how far east of Oakridge it is blocked off when the tunnel is closed.
If you do travel Rt. 58 stop and walk through the Lowell covered bridge. You drive over the new concrete bridge to get to the parking lot for the old covered bridge.

Thanks for all the information and ideas. I am checking out each one. We've eliminated the coastal ideas because we've spent time there previously.

Mms, I appreciate the suggestion of Silver Falls State Park. A friend had mentioned it also, and it looks wonderful. Just the perfect activity to stretch our legs. The map app shows it is 4 1/2 hrs or more from Ashland and 42 minutes from Salem.

We are now thinking we might just visit Crater Lake for the day and then drive on to Ashland (or down to Weed) for the night before driving home the next day. Are these highways OK at night (Hwy 62 or Hwy 97)?

Does anyone have food recommendations for Sisters?

There are about 4 different routes to drive from Portland to Sisters. The Gorge is beautiful (we were there years ago) but there is no lodging available in Hood River. Which would be your 1st, 2nd, 3rd choices for the drive?
We still have to find a place to stay between Portland and Sisters - a Saturday night, so not so easy.

Go to Crater Lake. No lodging available. Suggestions?</>

Keep calling. Somebody will cancel. Evening is a good time to find a cancelation.

HTTY

PS Smith Rock and Crooked River are our two favorite spots near Bend. The drive from Bend to Sisters affords great views of The Sisters and Mount Jefferson.

Check out the Oregon Garden Resort - close to Silverton and Silver Falls State Park-

http://www.moonstonehotels.com/Oregon-Garden-Resort.htm

If want to do the hike this might be a place to stay between Sisters and Portland.

In Sisters I like to eat at the Sisters Hotel - nothing off the charts, just good casual food- they usually have marionberry cobbler.

For a special dinner you could go to Black Butte Ranch - a short drive from Sisters - but dining room has great views of the Three Sisters mountain range from dining room. Am sure you would need a reservation.

As I was submitting my post, this piece of misinformation caught my eye: there is no lodging available in Hood River.

Last week we stayed in a lovely new room on the third floor of the east wing of the Best Western. The room had all the amenities one might want, including a balcony overlooking the Columbia. We also enjoyed a complimentary hot breakfast served by a delightful woman in a cheerful riverside dining room.

HTTY

If you want time to pass slowly - very slowly - spend a night in Weed. There is truly no there there.

You only save about an hour's driving time by staying in Weed instead of in very cute Ashland which has a number of good places to dine/stay.

Food rec for Sisters: Bronco Billy's aka Sisters hotel.
Having eaten at several other places in Sisters, Bronco Billy's is the best.

Don't know your budget - but if you can get in on Sat night - Timberline Lodge on the slope of Mt. Hood is a classic (if I haven't mentioned it in this blog)- and there are other B & B's at nearby Government Camp - or the Highlands Inn in Welches is very nice, which is now called Reort at the Mountain? Tried to buy it (with a much deeper pockets partner) - a few years ago - and dag-nabit - if these people didn't beat us out.

Just love the setting.

http://www.theresort.com/home_history.php

elnap29--45 minutes is very generous from Salem to SF. I am not a leadfoot by any means and it takes me 30 minutes tops from downtown Salem, and that is if I hit every stop light As for staying in Weed, we have done that often on roadtrips. There truly is nothing to do there, but if you need a cheap place to stay and arrive late and leave early, it works. Believe it or not, the Motel 6 there is pretty good. It has been redone in the last few years and suits us just fine. In Sisters, our favorite place, and has been for over 40 years, is the Ski Inn. It is a total dive, but is really good. Locals say it is the best breakfast in town, which I believe. Their burgers and shakes after a day of hiking are pure bliss, lol!

Geesh. I guess I have to dig out the thread on Ashland/Rogue Valley Restaurant, of which there are many, from Fench to Buffalo/Elk/Venison burgers.

And if you want to stay at a very nice resort - in my old home town of Klamath Falls, Oregon (Crater Lake is in large Klamath County) - check out the Running Y Ranch - or beaucolic Lake of the Woods.

http://www.runningy.com/ and http://www.southernoregon.com/lakeofthewoods/index.html

Thanks for all the tips. I've written down all the restaurant names for reference - this will be helpful!

I didn't mean that lodging in Hood River didn't exist; it's just that everything is all booked up because it's for a Saturday night. I had also checked with Oregon Garden Resort a few days ago - no availability there either. I'm hoping we can just "wing it" and figure something out as we go along. Still trying to decide the route between Portland and Sisters.

While Timberline Lodge and Running Y look nice, I am hoping to spend a little less on the Saturday night and the Tuesday overnights, as this is supposed to be our 'inexpensive trip' so we can save up for a European trip next year. We started out planning a tent trip but it has morphed into something different.

If we stop in Weed, it is only to be closer to home on our last night, not for any other travel value. Thanks, mms, for letting me know about the Motel 6; I probably would have disregarded it otherwise. Just looking for a quiet, clean comfortable bed.

Thanks, HTTY, I had also tried the Best Western you mentioned - but no availability. We are adding your info on Bend area to have with us.