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Oregon itinerary feedback- early Sept

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Husband and I are planning 2 week trip to Oregon early Sept. We visited years ago and spent time on Northern coast and Columbia River Gorge. This time we'd like to do more hiking and road biking (not mountain biking) and exploring other parts of the state. This is the itinerary so far:

Sun: arrive PDX early afternoon, drive to Eugene. Spend 2 nights exploring city.

Tues: drive to Crater Lake Lodge. Have reservations at the lodge for 2 nights. Hike the area. Maybe do some biking - haven't done much research into this yet. Heard a nice ride was around Indian Lake? We bike a lot - have done century rides and biked through Andalusians and Tuscany but I have heard Crater Lake is difficult riding. If we can't bike, I'm sure there's plenty of hikes to do.

Thurs: Drive to Bend. Rent bikes again and explore the area and hike. Have heard there are numerous activities within driving distance. Spend 4 nights in this area.

Mon: Drive to Hood River and spend 2 nights. Ride bikes east toward the Dalles area - heard there are many orchards and farms that bikers visit.

Wed: Drive to Portland and spend 3 nights. Have seen all the falls last trip but will stop again - they're beautiful!. Will leave from PDX on Saturday.

My questions: do we really need a car in Portland? Would love to drop it off when we get there and use public transportation - how easy to get to the airport without a car?

We had toyed with staying at Timberline Lodge one night but will it be too cold mid-September? Driving from Bend to Mt Hood and then to Hood River is a lot of driving, even over a few days. Would love to fit in at least a visit to Mt Hood but it seems to be out of the way in our itinerary.

Any feedback? I know it sounds like a lot of driving but this is how we do our vacations. We want to see as much as we can - DH has only 1 stipulation: we spend at least 2 nights at a hotel before moving on!

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