Oregon Vacation Ideas...Need Some Help

[Haldon]

I'm planning on taking a vacation to Oregon with my lady at the end of May 2015.  Neither of us have ever been, and I've done a good bit of research.  However I don't know anyone who's ever been to Oregon, so I was hoping that some of you locals, or folks who have gone, can give me some solid advice, or shoot me in the direction of some good ideas.
We are planning to do 9-10 days.

Here are some general questions that I've got:
THE COAST: How many days should we plan to spend doing to Upper and Central Oregon Coast? (We're thinking of doing Ecola State Park/Cannon Beach, neahkahine mountain hike, 3 capes scenic loop, cape perpetua, and sand dunes park for some dune buggying).  Can that be done in 2 1/2 days?  Any hikes or things to see that you'd recommend

CRATER LAKE: we'd really like to go and spend a day at Crater Lake, but I've heard that many of the roads may be closed, and park areas limited due to lack of snow melt.  I've always wanted to go here though.  However I wouldn't want to drive all the way over there and be let down if all things were closed.

WINERIES: my girlfriend would really like to spend sometime in the Willameete (sp?) Valley.  Any recommendations for places to definitely see, or definitely stay away from?

PORTLAND: we are hoping to get about 2 full days in the city.  We're interested in hitting up some breweries, maybe taking a bike tour, seeing the Japanese and/or Chinese Gardens, and making sure to get some of that great Portland cuisine we've been hearing about.  Any suggestions about places that we just absolutely have to drink at/eat at?  Or places that we must visit.

WATERFALLS: I loooooove to hike, and seeing as how the new MMJ album is titled Waterfalls and will have come out just, I'd love to experience Oregon in all its natural wonder.  I've read that all along US-30 there are tons of places where you can hike and see gorgeous waterfalls.  I'd like to do Multnomah falls and oneonta falls.  I'd also like to do a Wildflower hike, as I've heard that they are quite abundant and beautiful around that time of year.  I've read that Tom McCall Preserve in Rowena is nice.

Lastly, since the conservative and oppressive powers that be here in Florida can't find it in their hearts to legalize marijuana...even if its for beautiful children dying of brain cancer....I'd like to take full advantage of Oregon's liberal/progressive/reasonable views on marijuana.  Any suggestions as to top shops to visit?

Ok, thats it.  If anyone's got any thoughts, advice, guidance, ideas, comments, I will welcome them all. 
Thanks a lot friends, and I hope to see you all at a jacket show soon.

Your Friend,
Haldon

[walterfredo]

Not from OR, but a west-coaster and have spent a lot of time in the PNW over the years.  Some additions to what you've mentioned...

-I really love Bend.  Great little (big) city with a lot to offer, IMO.  Beautiful area, lots of hiking, rafting, etc.  Although you maybe there in a bit of a 'tweener season between winter and summer sports.  And if you are a fan of beer in any way, Bend is the place to go, some of the best breweries in the country are located in/near Bend. If you make it there, highly recommend Boneyard Brewing.   

-beer places in Portland: 
breweries: if you like sours definitely hit up Cascade brewing (they make great non-sour beers too), Hair of the Dog brewing, Upright brewing, Gigantic, and about a meelion others as well, those are some of my favs though.

beer bars: belmont station and apex are great.  So many others too.

-Coos Bay, beautiful, check it out.

-I think it's usually in early June (and I haven't been in a LONG time), but the Oregon Country Fair (about 20 minutes west of Eugene) can be a crazy experience.  Lots of partying, old hippies, music, crafts, food, etc. 

-If you've never been to Seattle, may be worth a drive up there for a night or two. 

[vespachick]

Haldon, we are not weed legal until July 2015, so you'll have to drive up to Vancouver, WA.  It's only 10-15 minutes north to the dispensaries (Obama Cush comes to mind....).

Eating: Pok Pok, Beast, Le Pigeon, Noble Rot. 

Country Fair is outside of Eugene and is not until August EDIT: JULY, so.  You should just change your plans and come in August, so you can also enjoy Pickathon (first weekend in August).

So.Much.Beer.

I would avoid Willamette Valley Winery.  Their wine is not so good and they are jerks to dogs.  Wizzard probably has a lot of insight on the wine scene (I just drink a lot of it); she works at Anne Amie out in Carlton; you should look into the Dundee area, not such a far drive from Portland proper.

I've never been to Crater Lake.  Those pics Tucker posted are indeed from Multnomah Falls, and is so worth visiting and easy drive from Portland. You might consider visiting the Maryhill Museum of Art and the Maryhill Winery, when you're out that way.

The art museum in Seattle is awesome (SAM); they have a bunch of Rothko's.  That's all I need to know about it. ;)

PSA: Willamette: "will - am - et" is how you pronounce it.

EDIT: also, you know what is fantastic? The Glass Museum in Tacoma.  If you head up to Seattle you should stop there; there is a ton of Chihuly installations and they have a hot box demo studio that is pretty sweet to watch.

[rincon2]

Not sure where you are from, but if you want to see picturesque roads through rolling hills and pure greenery, and blue sky if you get lucky in the spring, plus quaint towns, some with lakes, then the coastal range between the ocean and the Willamette Vally/Cascades if fantastic. There are great campsites 30 miles out of Eugene that were vacant and cheap when I was there one June. Highway 58 leaves the city and right into the Cascades. You can do a one day loop and really get a taste of the mountains. In late June Crater Lake was still snowed in. The whole coast is worth it. East of the Cascades is kind of high desert, so it is a different world than what most think of Oregon. If you go into Newport on the coast, stop by the library and say hi to the librarian Sheryl. My sister. (Her only comment on the song Librarian was it was too long) 

[Haldon]

bump...could still use a bit more help/info/guidance/advice, if anyone's got some

thanks

[mdgsolo]

PM Me.  I live in Bend in the middle of the sate and know Oregon very well and would be happy to help..