Alright, I'll offer up a little different spin on your itinerary so you hit the spots you mention, just approaching it from the opposite direction.
- Friday, fly in and stay in Portland that night. Don't be afraid of the city of Portland. It's had some issues, but it's a lovely place to be in Sept. Consider
Inn at Northrup which is in NW Portland. Entirely walkable, lots of restaurants, old homes that have character. You'll encounter some derelicts, but you'll be fine. Happy to recommend spots to eat/drink.
- Saturday, head down the Gorge taking your time to get a hike in or two. You can visit Multnomah Falls - and you definitely should, even if you just grab some photos - but for a hike, I'd strongly suggest
Horsetail Falls, which allows you to walk behind a very powerful fall. It's awesome. You can hike to the top or just go behind the falls and head back on an easy hike. Other ideas - Latourell Falls and Angel's Rest, which is a killer hike to the top with amazing
Gorge views. Angel Falls is a moderate hike with some elevation, but if you're feeling it, the payoff is outstanding.
- Continue east to Hood River, OR and stay there. This is home to some of the world's best wind surfing and kite surfing and watching these guys fly around the Columbia with a cold beer is a lot of fun. You might see a bald eagle or two hunting for fish. There are a BUNCH of great spots for food, beer and wine. You can even go across the river on the Hood River Bridge to
Everybody's Brewing for a pint and amazing views of Mt. Hood. Plenty of hotels around Hood River, but you can look for ABnB too if you like. Some really neat places there with awesome views. Other suggestions: pFriem Brewing, Double Mountain Brewing, Naked Winery, Cathedral Ridge Winery. Full Sail is there, but it's not my favorite....
- Sunday, head up to Mt. Hood on 35 - this is a really neat drive up to Hood and you should check out
Timberline Lodge which was featured in The Shining and was part of the Works Progress Admin under Roosevelt to get us out of the Great Depression. Hikes all over, plenty to check out and explore, but visiting Timberline is really a must. You can spend as much time here as you like and stay there too, but unless you just fall in love with the mountain, I'd continue your journey on to Bend via 26 to 97. Before you get to Bend, stop off at
Smith Rock State Park. Other ideas - Lava Butte, Lava Lands, etc. The High Desert is incredible, so I think spending Sunday night and Monday in Bend is a great idea. I *LOVE* Bend. There is so much to see and do and there are probably a dozen or more breweries that have cool outdoor areas with cornhole, horse shoes, etc. I might even consider TWO nights in Bend so you can get that full Monday in there.
- Early Tues, head out to Crater Lake. I just want to make sure you get enough time here to really experience Crater Lake. I would recommend the
boat tour, which I've not done, but my wife has and said it was one of the coolest things she's done. From Crater Lake, you can then hit Umpqua Hot Springs and Toketee Falls which are very close together. You could even stay around the area at
Umpqua's Last Resort, which looks really cool. Do a little glamping!
- Wed morn, head down to Jedediah Smith Redwoods State Park. About 3 1/2 hours away from Umpqua. Man, I don't know what to say here. The Redwoods are magical. I'd not want you nor anybody to race through seeing these magnificent trees. You can find a million cool spots around here, from tourist attractions like
Trees of Mystery to hidden hikes, no matter where you go, you're going to be in awe of the trees. Find a place there to stay Wed night - look for something IN the Redwoods.
- Thurs, head up 101 taking your time to stop and appreciate the glory. I'd target Yachats which is about 4 hours north of Jedidiah. Gold beach is neat - there's specks of gold in the sand and it sits at the mouth of the Rogue, which I'd love to explore one day but haven't yet. You'll go through Bandon, which is a golf paradise. Florence is a neat coast town with giant sand dunes you can check out. Yachats - man, this is the chillest place on the coast. Get a meal at
The Drift Inn. The back patio is fabulous. Food is outstanding. Service is friendly, which is in short supply on the Oregon Coast. Yachats is a little south of Waldport, which is where we like to vacation. Beaches are not crowded, there's cool driftwood logs, the weather is a touch warmer, just a really cool spot. You might not want to leave! Stay there that night, whether Yachats or Waldport, you'll be okay. Cape Perpetua, Thor's Well, Devils Churn, Amanda's Hike...all right there and all worth your time.
- Friday, continue your drive up 101 to Cannon Beach. There's an aquarium in Newport that's neat, but I'd skip it. Depoe Bay is prime whale watching, but can be a bit of a headache parking and walking around. Have lunch at the
Pelican Brewery in Siletz Bay. This is the newest Pelican, built in 2022 and it's so cool. Big wrap around deck, views of the bay, great beer and food. A bit pricey, but worth it. Pacific City is cool - also has a Pelican with great views of a haystack rock - there's a neat beach in Oceanside where you can hunt for agate rocks. Tillamook is where the cheese factory is, but I'd skip that. It's not worth your time - just get some of their cheese or ice cream at a store. It's a tourist trap. On to Cannon Beach to stay Friday night.
- Saturday, take your time at Cannon Beach. It's a gem. It's a 90 minute drive from Cannon Beach back to Portland, so don't be in a hurry to get back. Yeah, you can go all the way up to Astoria and that might be cool if you're a Goonies fan or Kindergarten Cop. There's a cool museum there, the Lewis and Clark National Park, great food and beers. Also about a 90 minute drive back to Portland. Skip Seaside, OR. Stay in Portland Sat night, fly back Sunday.
You miss Silver Falls and Abiqua Falls, though you COULD theoretically hit them real fast, but that's not the goal. For example, if you REALLY wanted to hit Silver Falls, it's a long hike that'll take you hours to see complete the full loop and see 10 different falls.
Just another way to look at your journey. You can't go wrong. It's lovely here.
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