Wife and I are going to hit Oregon by plane in a few months.

Planning to start in Bend or that town near it... Planning to leave by plane on the lower west coast a week later.

Items to hit a wine tasting if there is any to be had. Mabey some white water and of course lots to eat.

Need to know the best places to take in for 5 days

Thanks

Time to be had early May
Your help matters, need knowledge here...

My I suggest http://www.visitbend.com

Flying into Bend will add cost to your trip...rental car?
Drive from PDX...about three hours and a nice drive. Great area in Bend, all the food you'd need, not really wine country but hey, there are bars and stores.

Wine country is Willamette Valley south of Porkland and expanding to the coast and Cascades. May is early for wine season but call ahead to see who's open.

You could head south on 97 out of Bend and make it into Nev/Cali on your way south. I'd choose that over I5 but I like backroads.

Coming from Colorado...might consider Hwy 101 along the coast if you haven't seem much coastline. Could always come back into I5 at seveal spots and a 1.5 hour trip.

Lots of travel Oregon web sites to help you plan...Google is your friend.

whitewater aint happening until summer!

Bend is good if you ski or snowboard. Not much going on in winter, besides great beers etc. 

You need to know that if you want to hit the valley for wines... or fly into PDX and drive, you'll have to go over mountain passes. Right now theres a lot of snow!!

Gotta second what folks above said.  Fly into PDX and drive from there, the time you'll save not F'ing around changing planes to get into Bend you could spend on a very scenic drive.

One possible route would be I-84 east to Hood River (see a little of the Gorge, Multnomah Falls, good eats/brews in Hood River).  Better yet, take SR14 on the Washington side; it's easy to get to from PDX and IMHO much more scenic, if a bit slower, than 84.  You can cross the river again at Hood River.  Then south on 35 thru the Hood River Valley (very scenic, backside of Mt. Hood), link up with US 26 and continue south to Bend.  

Once you've had your fill in Bend, take US 20 west back over the Cascades, 22 up to Salem, keep going a little further to 99W and head up into "wine country" from there.  You can get to the coast several different routes from along 99W, all without having to pass back through any major cities.

US 97 south of Bend is interesting the first few times but isn't exactly the most scenic; well not that long-ass straight stretch in the middle, anyway. But it does make for a quick trip into Norcal from central OR.  If you jump over to the Rogue Valley before hitting Klamath, you can take 195 to the coast.  I always liked the drive from Grant's Pass out to the coast.

Oh, and one more thing.  If you decide to visit "wine country", please don't get lost and turn around in my driveway.  I'm getting really tired of that shit.

Interesting...

Good tips I see here. Thanks folks

Yeah, whitewater is going to be snow run-off and ice-fucking-cold until the middle of summer.  Running the Deschutes around the Maupin area is a hoot, but seriously, you're not going to enjoy it unless you rent a drysuit if you hit the water before the 4th of July.  

We're having an unusually cold and wet winter this year.  Others who are more local can chime in with better stats, but I think that Bend has had like 50" of snow since Christmas and I don't think the temperatures over there have had a daily high above 32.  That is to say, most of that snow is still on the ground.  

Oregon is a state where what you go do outdoors is often dictated by the seasons.  If you give us a more specific time than "a couple of months from now" I'm sure you'd get some better input.  Bend is beautiful and popular for good reason, even with all of the snooty assholes who have moved there over the past two decades (apologies to any non-snooty assholes living in Bend, you're not the ones I'm referring to).  

The suggestion above of flying into PDX and renting a car is something I'd echo.  One of the great things about Oregon is you can go from the coast, drive though the Willamette Valley, cross over the Cascades, and then be in the high desert in a couple of hours and during that whole drive there's something impressive or beautiful to see out of your window.  Get out here and see it now before the fascists in Portland ruin this state any worse.

Just 10-15 min south of Bend is Sunriver.  A sizable resort property with a ton of vacation rental options, ranging from simple, intimate cabins to large, luxury custom homes.  Miles and mile of cycling trails, golf, fantastic observatory, etc. etc.  Really nice spa too if you're into that sort of thing.  Worth grabbing a copy of the book Bend Over All (LOL yes, I know) that outlines pretty much every sightseeing, hiking, water and other outdoor activity imaginable within a 2 hr or so radius of Bend.  Plus some really sweet outdoor shooting spots (Google Earth the area - they will be pretty obvious...just observe the usual good judgement, safety and pick up after yourself).  Bend also has some neat restaurants.  If you like the nicer bistro-type stuff, have taken wife to Ariana quite a few times and it's been consistently good, both food and service.

Been coming to SR with family on and off since 1983 and it's stayed near and dear to us over all these decades.

SunRiver is fun.  Rent a house for a few days as base camp for mountain fun.  I can tell you exactly what house to rent too! 

Columbia River Gorge National Scenic Area is very cool but better in the summer.  Especially kite boarding in Hood River (again a summertime activity).
Rent some snowmobiles and head up to Paulina Peak (Central Oregon near Bend).
Crater Lake is worth a look.
Oregon Coast is fun for storm watching in the winter.  I especially like Astoria.  Great Maritime Museum and Astor Column, Fort Stevens and Fort Clatsop (all a must see IMO).
Dundee is a great area for wine plus it's near Spirit Mountain Casino (okay but I'm not a gambler).
Portland is okay for a visit.  I guess.  Beautiful city but a disgusting liberal cesspool at the same time.

Have fun.  You may want to come again in the summer after seeing this beautiful state.

Another vote for Sunriver!  Close to Bend, great hiking trails, and relaxing.  Hit that up for a few days, then head about 2 hours west to Eugene where you can hit King Estates and a few other wineries out in the country.  If you're a baseball fan, you can check out the Duck baseball team that time of year and walk around the stadium compound.  Then fly out of Eugene...there is an early morning United flight direct to Denver.

Fly into PDX, drive to Bend for a day or two.  The High Desert Museum is neat, spend a morning there.  

Next drive North to the Gorge, stopping at Smith Rock and 'the bridge' (Peter Skene Ogden park) over the Crooked River.

If there is any WW rafting, Maupin is a good place to go and  is on your way.  Small town with overnight lodging.  Be sure to call before you plan on rafting the Deschutes can be really cold (it's the same river that runs through downtown Bend).

Stop in Historic Downtown The Dalles, see the end of the Oregon Trail, eat at the Baldwin Saloon.  Wineries are popular in the Gorge.

Go west 20 miles to Hood River, stay for a day or two.  Lots of kiteboarding and windsurfing going on.  Also be sure to stop in HR and see WAAM museum (Western Air and Auto Museum)- very cool and everything runs.  You can make a trip to Timberline lodge for lunch.  You might get snowed on.

Tons of good hiking through the Gorge.  A lot of it is on your way to Portland along the historic highway (Rt 30) but check first there's a section that is closed due to avalanche and no opening date posted so far.