We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

New to Oregon and looking for some help with itinerary!

Elgin, Illinois
Level Contributor
40 posts
New to Oregon and looking for some help with itinerary!

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!


Eugene, Oregon
Destination Expert
for Eugene, Springfield
Level Contributor
9,933 posts
200 reviews
1. Re: New to Oregon and looking for some help with itinerary!

What time will your flight be arriving at PDX? You should probably not plan on getting to Crater Lake that day. You'd be better off aiming at Grants Pass or Medford for the night (at least a 5 hour drive from PDX) and seeing Crater Lake the next day. Go in the south entrance of CL, drive the rim road and exit through the north entrance to Diamond Lake and #138 North Umpqua Scenic Byway to Roseburg (stop and see Tokatee Falls). From Roseburg, continue on the #38 South Umpqua Scenic hwy to Reedsport. These roads parallel the beautiful Umpqua River. Just before you reach the coast, stop at the Dean Creek Elk Viewing Area.

Then, head north on 101...and get the coast done before the wine country. Spend a night in Yachats or Newport. Turn east at Tillamook and it'll take you right into the core of the Willamette Valley wine district.

This eliminates the northern coast (Cannon Beach, Seaside, Astoria) unless you can squeeze a couple more days into your itinerary. Your Sunday and Monday in Portland, with daytrips on the Columbia Gorge/Mt. Hood Loop and seeing Portland itself look good.

Longview, Washington
Destination Expert
for Mount Rainier National Park
Level Contributor
2,590 posts
139 reviews
2. Re: New to Oregon and looking for some help with itinerary!

It would be hard to improve on o'poppa's Itinerary. Go for it! There are also very nice wineries in the Umpqua Valley near Roseburg. Google Umpqua Valley Winegrowers Association.

3. Re: New to Oregon and looking for some help with itinerary!

-:- Message from TripAdvisor staff -:-

This topic has been closed to new posts due to inactivity. We hope you'll join the conversation by posting to an open topic or starting a new one.

To review the TripAdvisor Forums Posting Guidelines, please follow this link: http://www.tripadvisor.com/pages/forums_posting_guidelines.html

We remove posts that do not follow our posting guidelines, and we reserve the right to remove any post for any reason.

Removed on: 07 June 2014, 06:17