Hi all! I am new to looking into traveling to Oregon, but I am not new to TripAdvisor and I know I can look to this site for great help for you! Labor day weekend my boyfriend are planning on taking a trip throughout Oregon, arriving Wednesday in the afternoon and leaving Monday evening. Just looking for a little advise on my 'loose' itinerary. We are interested in gorgeous scenery, great red wines, and hiking. There is no necessity to stay in fancy expensive hotels because we figure we will be spending most of our time outdoors. Here is our 'plan', if you could call it that lol, so far...
Wednesday - arrive from Chicago and take the drive down to Crater Lake. I understand there is little hotels available at the last minute so this leg of the trip is still up in the air. Any advise would be great.
Thursday - Explore Crater Lake and in the evening drive up to some vineyards to stay the night and explore Friday. I have heard the Wilmette Valley has the best vineyards... Any advise on wineries or where to stay? Dundee and Newburg have been mentioned but I am still a little confused on where the must see/taste wineries are.
Friday explore the vineyards and stay the night since we won't be able to drive!
Saturday - Drive some of the coastline (up the 101 I think its called?) and catch some gorgeous views! Any must sees on the coast? I was looking into Haystack rock, Florence Dunes, and Oswald West State Park... Just wondering if these are plausible in a day... We would stay somewhere on the coast line this night... Any suggestions are great!
Sunday - - Head early to Portland and check into a hotel here... Explore I think its called Multnammah? Waterfall and try to make it to Mt. hood or Mt. St. helens... I do not know if this is plausible in one day or not to see the waterfall as well as one of the mountains.
Monday - Explore the city of Portland during the day before flying home. Any must sees for an afternoon in Portland?
Any advise at all is greatly appreciated. I understand the information I provided is a little vague So if you have any questions please don't hesitate to ask! Thank you sooo soo much!