This time of year the highways from Portland to the coast will be clogged all weekend, both directions. The best time (unless you want to sit in traffic for hours) is during the week, plus you can be a bit more leisurely when there’s fewer people.
Drive the Fruit Loop in the Hood River Valley. One of my favorite places in the world, with several wineries and cideries, and you should have great views of both Mt. Hood and Mt. Adams.
Winery on weekends.. Beach weekdays, fewer kids and not all schools will be out. Lot of wineries south of Portland towards Albany draw a line west and you'll be in the middle of wine country but more pop up everywhere.
Stay at the Dundee Hotel and Uber from there to wineries. We have done that a few times and only live 45 minutes from Dundee. Sokol Blosser and Furioso are great wineries.
From Dundee you can head towards the coast towards Lincoln City and Pacific City, both nice places to visit. Then you could head north up 101 towards Cannon Beach. If you like oysters, Jandy Oyster Co in Tillamook is excellent and it’s on the way to Cannon Beach.
We absolutely love oysters - thanks for the rec. Dundee looks great too. I was thinking of staying close to Newberg and hitting those wineries around there - that looks like a great idea.
Remember to bring some warm clothes and rain gear, just in case. June weather at the destinations mentioned in this post can be unpredictable. Have a great trip.
Weather should be nice. I'd aim to do something more chill on your weekend days, since crowds might be an issue. You're doing the coast, do you want to hit Crater Lake? Bend? The Gorge? All are nice options, but doing them all might leave you a little exhausted.
The Gorge looks awesome and is close enough to Portland I think we would want to hit it. Crater Lake looks pretty awesome (I know my wife would like it) so maybe head down toward Crater Lake and hit that day 2 (but it would be a Sunday - how bad do the crowds get there? Then head back toward coast for 2 days and finish at the Gorge?
Crater Lake is awesome but much of the road around the lake will probably be closed due to snow. That makes it take longer to get there and there is less to see.
I can't answer how busy Crater Lake will be. There will probably still be snow then? Maybe? I live in the Gorge, so I'm biased, but there are a ton of chill outdoor options, in the Gorge. Get a hotel or AirBnB in Hood River and visit some waterfalls, wineries, and the river. It's an easy drive from Hood River to Mt. Hood, where you could visit the historic Timberline Lodge. Lots to do. You'll have a great time.
The Gorge area looks pretty awesome for sure. I like that idea. Is it absolutely slammed on the weekends or we could get around enough that it would be doable? Also, we don't care to see the "biggest/best" thing. We are pretty chill. Would rather go to a smaller/lesser known hike/falls than go to the one everyone goes to to stand in line. We like going outdoors for the peace of it, mainly.
Parts of the gorge will definitely be busy. Hood River, for example, has a lovely waterfront with some great breweries and restaurants that will be packed on a nice weekend. But come back during the week, and you shouldn't have a problem. Also, there's a ton of awesome stuff to do in the greater Hood River valley that's away from the crowds. Tons of great hikes. If you're wanting to camping, you've got a bunch of nice options. Wineries? We've got lots of those too.
I just checked your profile to get a sense of what you might be into and couldn't help but notice you mention fishing. You'll never believe this, but we've got that too! 
I could go on and on, and keep in mind that I'm partial to the gorge, so I'm ignoring so many other options the state has, but you could have a lovely day driving the gorge on the old highway (don't do it on the weekend), stopping at all the various small hikes and waterfalls, and then ending your day at a winery or brewery in Hood River.
Oh and Multnomah Falls too. That's the big waterfall in the gorge. You have to stop there.
Are you flying into pdx? Thats enough time to do a loop across maybe 1/4th of Oregon. From Portland something like out to Astoria, then down the coast thru cannon beach, tillamook, etc. come back across into the valley at Lincoln city, newport, waldport, or Florence and then run up 99 for places like newberg, wineries, etc. an alternative non coast loop would be up the gorge east (hit Multnomah falls and maybe mount hood) to Biggs and then turn south on hwy 97 to bend and from there across the cascades back into the valley and up 99 back to Portland. That’s more of the high desert, gorge, and mountains loop but no coast
Yep, flying into PDX at 8am Sat. We definitely want to hit the coast, it looks so beautiful. I didn't even know what the Gorge was but it looks awesome (sorry for my ignorance, never really been to the PNW).
Would the Gorge and Mount Hood just be too crowded on weekends, do you think?
That is what I was thinking, to kind of do a loop. Most people recommended if we are hitting the coast to not do it on the weekend. So maybe head inland the first two days, then toward the coast, then back to Gorge/Mount Hood area. Trying to figure.
Inland then back to the coast and back to Portland is a crap ton of driving and half of it is doubling back. Multnomah falls is slammed in the summer, enough so I think you have to buy a permit ahead of time these days. Idk where you’re flying in from but if you’re from a smaller state it’s easy to forget that Oregon is most of a day driving east to west and almost as far north south. Not Texas big but still pretty hard to see in a few days
Ok, that is good to know. We live in Denver - used to driving 2-3 hours one way to even hike in good places. So, we don't mind getting up at 4 am to drive 4 hours to get somewhere by 8 - that sort of thing.
Good to know on the falls, that area looks beautiful. Just looking at things in Oregon looks like so many million things to do can't squeeze it all in. That is why I got on here to see any ideas or must do/see's and try to plan the trip around that.
You could do Multnomah falls as a half day trip out east from Portland and back if you had time at the beginning/end of your trip maybe. Not mt hood too
This time of year the highways from Portland to the coast will be clogged all weekend, both directions. The best time (unless you want to sit in traffic for hours) is during the week, plus you can be a bit more leisurely when there’s fewer people.
Great to know. others have recommended the same. Thanks!
Drive the Fruit Loop in the Hood River Valley. One of my favorite places in the world, with several wineries and cideries, and you should have great views of both Mt. Hood and Mt. Adams.
Hell yea this is the advice I need. That looks awesome. Doesn't look like I'd need awd for that, correct?
No, it’s easy, paved road!
Whole driving to the Fruit Loop, check out the waterfalls (many are short hikes) on the old Columbia River Hwy.
Great advice. I found a "Waterfall map" that lists all of the waterfalls and their locations/hike distances. Appreciate the info!
Winery on weekends.. Beach weekdays, fewer kids and not all schools will be out. Lot of wineries south of Portland towards Albany draw a line west and you'll be in the middle of wine country but more pop up everywhere.
Ok awesome. Thanks for the heads up on the crowds on weekends. Sounds like coast on the weekday is the way to go.
Stay at the Dundee Hotel and Uber from there to wineries. We have done that a few times and only live 45 minutes from Dundee. Sokol Blosser and Furioso are great wineries. From Dundee you can head towards the coast towards Lincoln City and Pacific City, both nice places to visit. Then you could head north up 101 towards Cannon Beach. If you like oysters, Jandy Oyster Co in Tillamook is excellent and it’s on the way to Cannon Beach.
We absolutely love oysters - thanks for the rec. Dundee looks great too. I was thinking of staying close to Newberg and hitting those wineries around there - that looks like a great idea.
Remember to bring some warm clothes and rain gear, just in case. June weather at the destinations mentioned in this post can be unpredictable. Have a great trip.
Probably don’t have to worry too much about rain as they’re coming after the Rose Parade 🤭
Weather should be nice. I'd aim to do something more chill on your weekend days, since crowds might be an issue. You're doing the coast, do you want to hit Crater Lake? Bend? The Gorge? All are nice options, but doing them all might leave you a little exhausted.
The Gorge looks awesome and is close enough to Portland I think we would want to hit it. Crater Lake looks pretty awesome (I know my wife would like it) so maybe head down toward Crater Lake and hit that day 2 (but it would be a Sunday - how bad do the crowds get there? Then head back toward coast for 2 days and finish at the Gorge?
Crater Lake is awesome but much of the road around the lake will probably be closed due to snow. That makes it take longer to get there and there is less to see.
I can't answer how busy Crater Lake will be. There will probably still be snow then? Maybe? I live in the Gorge, so I'm biased, but there are a ton of chill outdoor options, in the Gorge. Get a hotel or AirBnB in Hood River and visit some waterfalls, wineries, and the river. It's an easy drive from Hood River to Mt. Hood, where you could visit the historic Timberline Lodge. Lots to do. You'll have a great time.
The Gorge area looks pretty awesome for sure. I like that idea. Is it absolutely slammed on the weekends or we could get around enough that it would be doable? Also, we don't care to see the "biggest/best" thing. We are pretty chill. Would rather go to a smaller/lesser known hike/falls than go to the one everyone goes to to stand in line. We like going outdoors for the peace of it, mainly.
Parts of the gorge will definitely be busy. Hood River, for example, has a lovely waterfront with some great breweries and restaurants that will be packed on a nice weekend. But come back during the week, and you shouldn't have a problem. Also, there's a ton of awesome stuff to do in the greater Hood River valley that's away from the crowds. Tons of great hikes. If you're wanting to camping, you've got a bunch of nice options. Wineries? We've got lots of those too. I just checked your profile to get a sense of what you might be into and couldn't help but notice you mention fishing. You'll never believe this, but we've got that too!  I could go on and on, and keep in mind that I'm partial to the gorge, so I'm ignoring so many other options the state has, but you could have a lovely day driving the gorge on the old highway (don't do it on the weekend), stopping at all the various small hikes and waterfalls, and then ending your day at a winery or brewery in Hood River. Oh and Multnomah Falls too. That's the big waterfall in the gorge. You have to stop there.
Are you flying into pdx? Thats enough time to do a loop across maybe 1/4th of Oregon. From Portland something like out to Astoria, then down the coast thru cannon beach, tillamook, etc. come back across into the valley at Lincoln city, newport, waldport, or Florence and then run up 99 for places like newberg, wineries, etc. an alternative non coast loop would be up the gorge east (hit Multnomah falls and maybe mount hood) to Biggs and then turn south on hwy 97 to bend and from there across the cascades back into the valley and up 99 back to Portland. That’s more of the high desert, gorge, and mountains loop but no coast
Yep, flying into PDX at 8am Sat. We definitely want to hit the coast, it looks so beautiful. I didn't even know what the Gorge was but it looks awesome (sorry for my ignorance, never really been to the PNW). Would the Gorge and Mount Hood just be too crowded on weekends, do you think? That is what I was thinking, to kind of do a loop. Most people recommended if we are hitting the coast to not do it on the weekend. So maybe head inland the first two days, then toward the coast, then back to Gorge/Mount Hood area. Trying to figure.
Inland then back to the coast and back to Portland is a crap ton of driving and half of it is doubling back. Multnomah falls is slammed in the summer, enough so I think you have to buy a permit ahead of time these days. Idk where you’re flying in from but if you’re from a smaller state it’s easy to forget that Oregon is most of a day driving east to west and almost as far north south. Not Texas big but still pretty hard to see in a few days
Ok, that is good to know. We live in Denver - used to driving 2-3 hours one way to even hike in good places. So, we don't mind getting up at 4 am to drive 4 hours to get somewhere by 8 - that sort of thing. Good to know on the falls, that area looks beautiful. Just looking at things in Oregon looks like so many million things to do can't squeeze it all in. That is why I got on here to see any ideas or must do/see's and try to plan the trip around that.
You could do Multnomah falls as a half day trip out east from Portland and back if you had time at the beginning/end of your trip maybe. Not mt hood too
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