We are planning a circle tour of your great state in Late August, early September 2012.
Being from Florida and in our 70's, are not interested in hiking, too much beach, though the Oregon Coast is much different than our beaches.
Here is our Basic plan, subject to change, depending on the advice from you Fodorites.
Fly to Portland. Rent a car at the airport, Stay 3 days in Portland. considering side trip up to Mt Helena. The on to the Gorge area as far as Hood River or the Dalles via Interstate or historic Highway? . Then south to (Hopefully) TimberlakeLodge for a day or two, then on down to Bend, Crater Lake Area for 2 days, to include Rogue River Boats then on down to Crescent City to see the Redwood NP 2 days? Back up Coast to perhaps Florence, Yachats? 2 days, The to up to Tillamook, to see cheese factory and go to see Spruce Goose in McMinville, on to Wilmette Wine country (probably another 2 days)and back to Portland to fly home. Most confused on where to stay on the Oregon coast . More interested in History of Coast, such as Lighthouses, great quaint, scenic lodging & great seafood. Will there be any fruit available at that time of year?
Oregon 2 Week Circle Tour or Longer
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I think I would not spend 2 nights at Timberline and spend an extra day in Bend- there is a lot to see and do in the Bend area. Do you have a plan on where you are staying in Bend? I like to stay at Sun River resort which is just a short drive to Bend .
On the coast I suggest the B&B located at the Heceta Head lighthouse ( you actually stay in the lighthouse keepers house) I think its a great place to stay with an amazing breakfast in the AM. There is a beautiful beach- my favorite. I think the area between Florence and Lincoln City is some of the prettiest in Oregon.
I also like to stay at the Adobe or the Overleaf- Yachats- they are connected by a paved trail and on the beach. The Adobe is the least expensive, has a restaurant with great views and some units have a kitchen if you like to do your own meals.
I do recommend the drive to Mt St Helens- you can spend most of a day just doing that.
If you are hoping to stay at Crater Lake Lodge I suggest you start making reservations now as it fills us fast.
September is usually a nice month here - enjoy!
IMHO, you are missing some of the best Oregon Coast, history of the coast, Lighthouses etc. by not including the NW Oregon SW Washington coastal area.
Astoria on the Columbia River is worth visiting for the view of the longest bridge over the Columbia (4 miles), the Astoria Maritime Museum with facinating displays of the Coast Guard, rescues on the Columbia river, hx of salmon canning and a tour of the "Columbia", a Lighthouse boat.
http://www.crmm.org/
Consider staying in one of the Washington State Fort cabins (across the Columbia river bridge) on the Washington side (be sure to buy your do it yourself cooking suppplies at Astoria and be prepared to climb stairs to bedrooms)where deer are in your front yard and the ocean beach is close by and visiting the Fort buildings and their purpose in WW II at Cape Disappointment or my Favorite Fort Columbia
http://www.parks.wa.gov/vacationhouses/
Consider visitng a real Ocean Spray cranberry bog...or drive your car (4 wheel drive best in case you get stuck)rental on the the Longbeach ocean sand...one of the few places in the US left to do that like in the car commercials.
http://northwestplaces.com/trips002/1-Longbeach/Long100.htm
And do visit the North coast of Oregon (south of Astoria( for wonderful trip in history at Fort Stevens re: Lewis and Clark and the American Indians.
http://www.oregonstateparks.org/searchpark.php
http://www.oregonstateparks.org/searchpark.php?region=north_coast
http://www.oregonstateparks.org/park_179.php
Stay at an Oregon Lighthouse
http://hecetalighthouse.com/
Good advice above. I would make the route counter-clockwise. Portland first (1 day) with a day trip out to McMinville to the Evergreen Aircraft museum. Next day US 30 to Astoria and then south to stay at Cannon Beach. Next day, Tillamook, Oregon Aquarium just south of Newport and end the day at Coos Bay. The hotel I like there is the Red Lion. Take route 36 about 5 miles east from Reedsport to see some Roosevelt elk.
Next day, is your trip on the Rogue river Spend the night somewhere north of Brookings. Next day, Crescent City and the Redwood NP to see the big trees. From Crescent City, head to Oregon Caves and Grants Pass or Medford. Head up Rt. 62 to get to the south entrance of Crater Lake NP. Exit from Crater Lake by the north entrance. The north entrance is only 90 miles from Bend. Do your research on what you want to do in the Bend area. When you leave Bend go on 97 to Madras and US 26 to Government Camp to head for Timberline. Rt. 35 north to the town of Hood River is on the east side of Mt. Hood.
Take the time to see the waterfalls and Mt. St. Helens if you have the time.
I almost completely agree with tomfuller. However, I would stay at the Mill Casino if you stay in Coos Bay. Also, Reedsport is north of Coos Bay, so you would have to get to the elk lookout before dark. While, it is neat, it can be passed up due to time restraints. You can take the Jetboats out of Gold Beach (varying miles/times). From the North entrance of Crater Lake you could take the Cascade Lakes hwy to see more scenic areas (prettier then just taking hwy 97) up to Bend. Bend is a fun town. If you like beer and want something to do in town, the Deschutes Brewery tour is great.
You said not too much beach, but if you haven't seen Oregon beaches, I suggest taking your time through this area first. It is nothing like Florida (while I like Florida's because you can actually get in the water!). I am from the Southern Coast area, so my heart lies there and would skip the North, imo. My husband is from Central Oregon, so we love Crater Lake up to Bend. I don't think you would need much time in Mt. Hood other then driving up to Timberline, maybe staying a night and then driving back to Portland (or to Hood River then to Portland).
The gorge between Hood River and Portland is very nice with all the waterfalls. Depending on time, I would say out to The Dalles would be expendable.
Just reread your fruit question, fruit would be more in the Willamette Valley then other areas and probably more vegetables.
Whatever you decide, you will see absolutely beautiful country.