We are a family of four, kids are 22& 23, starting our road trip in Portland on July 18-27. We have 2nights confirmed in Portland. We want to see Columbia River Gorge, Mt hood, possible wine country, Bend area, and Oregon Coast. Realistically, how much of this can I see to do it justice?Also, I’m having trouble with where to head first after we leave Portland. What makes the most sense? I know there will be roadwork and don’t know how long it takes from one place to another. Also, what would be the best places to overnight on this road trip. Thanks in advance for any help!

If you head West to the coast you’ll then be heading down 101 South on the Ocean side. Then at Florence head East thru Eugene to the Bend area.
From there head up 97 and come back down thru the Gorge.
That’s a rough idea.

Thanks for your reply. Is this doable with the days I have?

Based on all you've written, and because you have those things so clear in your mind, I think you should begin by going east through the Gorge, likely all of the way to Maryhill, WA, which is a good turning-around point where you can see a full-size replica of Stonehenge against a scenic backdrop.

Then, backtrack to Hood River, and then make a beeline for Timberline Lodge, Mount Hood.

After that, pass through Madras on the way toward Bend, and when you've seen enough of Bend, go farther west via McKenzie Pass toward Eugene and eventually straight through to Florence on the Oregon coast.

That seems a good backbone for such a journey and you can fill-in the blanks.

I'm not very well versed on the subject, but we spent two weeks in OR (with a few days in WA) about a year and a half ago, and we visited many of the places you hope to. I wrote a trip report, which may or may not help:

https://www.fodors.com/community/uni...e-pnw-1135320/

Hi, I am also from Oregon. If you are packing, be sure to throw in binoculars in case the whales are near shore. I'm sorry I didn't see your post sooner. It appears you are following Northwest Male's itinerary?

While I like Florence and that coastline north, it's a question of how much more driving you want to do. If you haven't made all of your reservations for this trip yet, you also could come across the Santiam Pass and stay on Highway 20 all the way to Newport. Newport is a fun beach town with a working port, historic center, great lighthouse, excellent aquarium. You should find accommodations in Newport if it is on weekdays. If not, check at Otter Rock or Depoe Bay, but the largest city for accommodations in central coast is Lincoln City. Honestly if you know the dates, you should look for these in the evening and book them (when you have wifi at your current lodgings). Post back again if you have trouble. I can send you some ideas.... Be sure to stop on your way at Otter Rock and Depoe Bay and hopefully you will see some whales.

No one discussed your suggestion for wineries, but go north on 101 and then take Highway 18 following it up to McMinnville. There are many wineries in the region.

Thank you so much for your reply and many suggestions. Very kind of all of you to give me such great input. Bags are packed and I’m leavin in the morning connecting in DFW and then to Portland for the first 2 nights. Also, thanks for the heads up with the binoculars!