Personally I'd drop Bend and Crater Lake, not because they're not great destinations, but because they're a bit time-consuming given your schedule.

Instead I'd reallocate that time to the Columbia Gorge, the Hood River Valley and Mount Hood, and to more time in the Willamette Valley.

Hood River (also areas on the other side of the Columbia, too) is orchard country and mid-October ought to be good both for fall color and for great harvest scenes - apples on trees, etc. Farther up the Columbia, around Maryhill, you're getting into serious winery country, and, although the landscape is more sagebrush-y, in October you'll probably have good vineyard color, with blue skies and the blue river - really stunning. Don't miss the Maryhill Museum if you're spending a few extra hours in the area. www.maryhillmuseum.org

Then travel to the Willamette Valley (maybe go by way of Timberline Lodge on Mt. Hood) where there ought to be great fall color. Go on a covered bridge tour - http://www.oregon.com/covered_bridges - many of which will be glorious with turning leaves all around.

Play the coast by ear. It's around two hours from most points in the Willamette Valley; if you get a great day (or even a stormy one) it's a good destination. But inland Oregon has so much to offer, that in a week you'll still come up short.

How I would do this trip-your mileage may vary. Land at PDX, rent car, head east on I-84 to Multnomah Falls and the other waterfalls along the old US 30. After seeing the Columbia Gorge spend the night in Hood River (or Timberline). Day 2 head up OR 35 to US 26 and head for Madras where you will head south on US 97 to Bend. Spend some time in the Bend area before heading for Crater Lake. There are a few places in the Crater Lake area to stay without going back to Bend. If you exit CL by the north entrance, head west on 138 85 miles to Roseburg to head north on I-5 to Eugene.
Spend your time in Portland at the end of your trip.

The Pine forests of the Cascades are not really colorful in the autumn. The few Aspen and Big Leaf Maple trees are yellow.

A comment on Day 3 - Explore Bend, Crater Lake (stay in Bend)-- not a 1-day deal.

Instead, explore Bend - Lava Tubes and many other volcanic features plus much more - spend the night in Bend. Crater Lake is a separate trip and IMO given your timeframe, maybe not in the stars. Head back west to your itinerary from Bend.

If you could skip Eugene after Crater Lake, you could continue on 138 west from Sutherlin to Elkton and take 38 west to Reedsport to see some elk before you see the ocean.
Winchester Bay just south of Reedsport also has a couple of nice motels.

Thanks as always to the wonderful fodorites! (I love pre-trip planning on Fodors! )

So is fall colors not so realistic in mid-October? We could completely skip the Oregon coast this time and spend more time in the Mt. Hood area and also do Crater Lake. One consideration is: my in-laws might be going with us and while we will definitely visit Oregon again (I know we will love it!!! ), this might be my in-laws' only trip. So I feel like Crater lake should be part of the itinerary. Would this work?

Day 1 - Portland (land, explore, overnight)
Day 2/3 - Drive to Hood River, The Dalles, Colombia Gorge (day trip - http://byways.org/explore/byways/2141/itinerary/53147)
Stay in Timberline? Mt. Hood?
Day 3/4 - Head to Bend, explore Bend (stay in Bend)
Day 4 - Head to Crater Lake (stay in CL)
Day 5/6 - Explore Willamette Valley (stay in Eugene, Springfield)
Day 7 - Portland overnight
Day 8 - Fly out

I always vote for staying at one of our favorite places - Timberline Lodge - and you have a great view of the glacier looking up the mountain on one side of the lodge - and looking down the Cascades all the way to Bend on the other.

From Timberline to Bend is a nice drive - around 110 miles and easily in a little over 2 hours - and you go past incredible Mt. Jefferson - which most people don't even know about.

Do love driving from Crater Lake - out along hiway 138 - along the mighty Umpquah (the mouth of the Umpqua is huge!!! -seagoing liners reguarly go upriver a ways) - and the Elk Herd is a trip as well as the drive up the Oregon Coast.

From the Coast - you could swing back from Florence to Eugene.

It might be a long driving day but oh so beautiful.

There are also some wineries just outside/to the west of Eugene - and we love The King Estate, Sweet Cheeks , and we had a nice lunch overlooking the vinyards at the Hinman/Sylvan Ridge winery. http://silvanridge.com/

I still suggest Hood River for night 1. I hope you can get a morning flight into PDX. I would skip The Dalles. The best of the Columbia Gorge is from Hood River west including the waterfalls.
I don't know how much of the coast you want to see. How about going west on 138/38 and seeing the coast from Winchester Bay north to Florence seeing the Oregon Dunes. Head back east on 126 to see the wineries near Eugene.
There are places where you can ride a dune buggy on the coast if you don't like the idea of hiking up a dune.

There are some areas where the fall colors are beautiful - the area between Eugene and Sisters usually has some color, especially around Clear Lake- mostly vine maple - we don't have big trees like maple and oak out east. If you interested in a beautiful walk where you likely will see colors, walk around Clear Lake - wish I could post my pics of last year

I still feel like you're shorting the Willamette Valley if you're looking for autumn color.

If Crater Lake has to be included, what about spending the night in Bend, but visiting Crater Lake the next day and ending that evening in Roseburg or Cottage Grove instead of staying at the lake? Depending on the date, the Crater Lake Lodge may already be closed for the season (and it's no great shakes to begin with, frankly) and the other accommodation within the National Park (some cabins) are far from the rim of the crater, overpriced and pretty mediocre, plus I don't think there's anywhere to eat.

This is partly why I suggested skipping Crater Lake - its season is short and it's a long way from everywhere. Instead, if you want an easy trip to a pretty exciting natural wonder, a day trip from Portland or the Gorge to Mount St. Helens is a LOT closer and pretty doggone spectacular. Since it would be a day trip, you wouldn't have to break camp twice; stay someplace in the Gorge for an extra night. (Hood River would be my preference over Timberline Lodge, for pretty much the same reasons as Crater Lake - not the most comfortable accommodations but priced like they ought to be.)

Regardless, if you DID go via Bend and Crater Lake, ending up in Roseburg, Cottage Grove, or even Eugene would give you more time to explore the Valley, or even to swing out to the coast as a day loop from the Willamette Valley. Hwy 38 out to Reedsport is lovely; you could drive up the coast to Newport (see Heceta Head lighthouse, for instance) and end up back in the Valley (Corvallis or McMinnville, for example) and be in the middle of some lovely rural country, covered bridges, wineries, etc.)

To each their own I guess, but IMO - Mt. St. Helens (with it's broken top) isn't close to being in the same league as Crater Lake - as some consider Crater Lake one of the 7 natural wonders of the world.

And at Timerline Lodge - it's not about the comfort but the incredible setting.

There are also some scenic Aspen groves in Southern Oregon (such as by Lake of the Woods - between Medford/Ashland and Klamath Falls) - but not sure how they will be looking in October. Some years great and others - if there is an early winter - not so spectacular.

Check out this short Utube for the Aspen campgrounds at pristine Lake of the Woods - and a great view of Mt. 10,000 foot high McGloughlin - but the actual Aspen groves are about 10 miles away. http://www.youtube.com/watch?v=HmubaC_jYP4

Don't get me wrong - Crater Lake is marvelous. But like all things short trips like this involve tradeoffs. I'm only throwing out alternatives.

As for Timberline Lodge, yes, it's gorgeous and historic. However it's expensive and at night the view goes away, and in mid-October it's going to be dark pretty early and probably cold as hell at night and could even snow. Last year I think the first sticking snow was in the first week of October?

(In fact, I know the Crater Lake rim road closes usually by the end of October but don't know when it starts freezing or snowing - the altitude at the rim is pretty high.)

No idea of the ages of the OP's group, but logistics do matter at that time of year.

oooh! Lots of good info! The folks traveling in my group are my 6-yr old DS, 2 of us in our late 30s, the in-laws: late 60s. I'll check the weather conditions but this year it seems almost like winter will come late (but then one never knows!!). There is a kite festival on Oct 13-14 in Lincoln City - is this worth going to? I could restrict my tour of the coast for 1 day to include the kite festival (my son was excited about this) and then head on to Eugene and reverse the entire itinerary. Have to decide by this weekend to book hotels etc so keep the info coming. Appreciate all the good tips and recommendations.

Just south of Lincoln City is one of my favorite view places - Depoe Bay and you might see whales from the cliff at the Surfrider Resort. Check out: http://surfriderresort.com/

Lincoln City is under a 2 hour drive from Portland.

The next day - you could drive south from there (along one of the prettiest sections of the Oregon Coast) - to Florence and into Eugene - or even go a little south of Florence to Reedsport ( http://tinyurl.com/8e669fv, about 3 hours) - and take 38? - back toward and across I-5 along the mighty Umpquah River (by Southerlin/Roseburg) - and get over to Crater Lake that way.

It would make for a bit long - but incredibly beautiful driving day, and within half an hour? of leaving the Coast - there is a beautiful Elk Reserve where you could stop and have a picnic lunch to break up the drive.


BTW - there is still plenty of daylight at both Timberline Lodge and beautiful Crater Lake.

Just Go For It!!!!!

And here is a U-Tube for the Elk Reserve at Dean Creek, Oregon - by Reedsport. http://www.youtube.com/watch?v=lHUwySFjFtA

BTW - best if you bring some binos to enjoy the beauitful scenery all the more, including the magnificent Elk.

Awesome info!!! I will bring my 250mm lens!
I am an amateur photog, so I would love to take pics of elk, if I spot them!
Binos will be good for my son!
Thanks, all. Final plans will be put in place this weekend - will repost my itinerary then!

This is the more-or-less final itinerary.. if anyone has any comments, pls do let me know. We do have some leeway to move things around a bit but not much. Thanks for all the help again!

Day 1:
Fly to Portland (stay in Portland)
Day 2:
Drive to Lincoln City (2 hrs)
Check out the kite festival (http://www.oregoncoast.org/fall-kite-festival/)
Drive to Depoe Bay (South of LC) - stay in Surfrider resort (http://surfriderresort.com/)
Day 3:
Drive south from Depoe Bay to Reedsport along Hwy 101 (views of coastline - 3 hrs)
Lunch in Reedsport
Drive along Umpquah River on Hwy 38 - stop half hour into drive to see an Elk Reserve at Dean Creek, Oregon, maybe carry a snack picnic
Continue to drive to Crater Lake, OR (161 m from Reedsport ~ 3hrs)
Stay at Union Creek Resort near Crater Lake
Day 4:
Drive around Crater Lake, head to Bend (91 miles ~ 2 hrs)
Stay in Bend (Fairfield Inn)
Day 5:
Explore Bend and sorrounding area
Stay in Bend
Day 6:
Drive to Hood River (143 m ~ 3 hrs) - maybe stop at Mt. Hood
Stay in Hood River (Best Western Plus)
Day 7:
Explore Columbia River Gorge
Stay in Hood River
Day 8:
Head to Portland, stay in Portland (63 m ~ 1hr)
stay in Portland
Day 9:
Fly out of Portland

Your route looks good. What time do you get into Portland?
If you didn't want to rent a car immediately at PDX you can take the TriMet light rail in to Portland and rent the car on day 2. Take US 26 all the way to US 101 south. Make a brief stop in Cannon Beach to see Haystack Rock.
Make a stop at the Tillamook cheese factory for some great ice cream and maybe some cheese for your lunch in Lincoln City.
You might not see elk at the first pulloff at Deans Creek. Sometimes you see them about a mile east of the main viewpoint. I saw about 40 in 2 groups the last time I stopped.
Union Creek is not a Resort in the same sense as Diamond Lake.
There are a few old cabins and a small restaurant at Union Creek.
It is 91 miles from the north entrance station of Crater Lake to downtown Bend.
Which attractions do you want to see while you are staying in Bend?
Be sure to take Rt. 35 down the east side of Mt. Hood to the town of Hood River. Even if you don't eat or stay there, see Timberline Lodge.

Thanks again, tomfuller! I actually put down 2 nights in Bend thinking it would be close to the wineries but then realized its not! So now I just have to find things to do around Bend. If we didnt have the 6-yr old and in-laws, we might have done a day of white-water rafting or some such adventure. But instead we have to either find shorter hikes or something else to do... need input or more research. I will keep other pointers in mind - so nothing to eat near Union Creek? We should eat and then head there? How about at Crater Lake? Do we need to pack lunch/food and head there?

Stock up in Roseburg before heading east on Rt. 138. You can get a good meal at Steamboat. You may or may not get a good meal at the lodge at Diamond Lake. I never stopped at the little restaurant at Union Creek. While in Bend,drive at least as far as Mt. Bachelor. If you decide to go further, Elk Lake would be good.
To the east of US 97, head out to the Newberry Caldera to see Paulina and East Lakes and drive up to the top of Paulina Mt. if the snow has not already closed the road. The top of Paulina is 7980' above sea level and is the highest point that you should try to drive to with 2WD in Oregon.
Also see the High Desert Museum about 5 miles south of Bend.

I think it sounds like a good plan. Between Bend and the metropolis known as Sun River - is the High Desert Museum (or close if I don't have the name right) - which is very interesting. Ah - here it is: http://www.highdesertmuseum.org/

Also - if you drive toward the two cute lakes - Paulina and ?? - there is a mountain flow of obsidian you can see (sharp glass like lava rock used by the Native Americans/Indians for their arrowheads) and you can drive to the top of Newberry Crater - which has a great view. http://tinyurl.com/3e6yf2t,


The only thing I would add is that on your drive north on 97 from Bend to Hood River - take an hour or so and head in 26 a little ways - and go up to see Timberline Lodge at Mt. Hood. http://en.wikipedia.org/wiki/U.S._Route_97_in_Oregon

Think you would really enjoy having a cold beverage and/or snack at the 3rd floor bar/lounge looking up at the Glacier - (Ram's Head Bar - http://www.timberlinelodge.com/visit/dining/restaurants-bars/rams-head-bar/ )and then from the front porch - look down the Cascades to see where you were (Three Sisters in Bend, Mt. Jefferson, etc).

BTW - don't forget to peek in the Blue Ox room. http://www.timberlinelodge.com/visit/dining/restaurants-bars/blue-ox-bar/

From Timberline on up to Hood River - is about an hour - and it's a very pretty drive as well. On a clear day - you might see this big mountain - Mt. Adams - across the mighty Columbia - which most people also don't know is that big and beautiful of a snow capped Cascade Cindercone.

http://tinyurl.com/8bqc9gj,

Just trying to enhance what TomF had said.

There is lots to do in the Bend area - Sunriver is a beautiful resort with great walking and biking trails- you can rent bikes there. After Labor Day most of the tourists go home and there are no crowds.

There are not many wineries around Bend but there are lots of brewpubs if you are into beer.

You can take the gondola up to the top of Mt Bachelor to get fabulous views of the area .
Sounds like you are staying at the Fairfield in Bend - I don't know that hotel but I suggest you take a look at the Old St Francis School- an old Catholic School turned into a hotel- its a very fun place to stay with a restaurant, movie theatre, and a Moroccan soaking tub. I know a recent Fodorite stayed there and loved it.

There are lots of short hikes to do in the area- the Deschutes River Trail is nice- and there is a nice trail right in Bend along the river by the Old Mill shopping area - its flat and easy and you can have a beer when you are done.

An interesting place near Bend is Smith Rock- world famous for rock climbing- there is a nice walking trail along the river and you can watch the climbers - I even saw one fall one day but was on ropes so no injury.

We have been having forest fires in the Sisters area so hope its all over by the time you arrive - air even in Eugene today is thick with smoke.

Be glad you are staying in Bend. The air quality in Sisters has been getting much worse in the last week. The Pole Creek fire has grown to over 16000 acres the last time I checked.
The Incident Command center is at the Sisters Rodeo grounds. I'm guessing they will be working on this fire through mid October.
The road in to Timberline I believe is off Rt. 35 a couple miles north of US 26. I am hoping the persistent smoke doesn't block your view of much of the Cascades.
Check and see what is playing at the Tower Theater in Bend when you are there.
Cheapest gas in Bend are the AM/PM Arco along 3rd St.
You get your gas pumped by an attendant in Oregon-NO self serve.
The other place to top off is at the Y in Madras where 97 and 26 split (Safeway) which also has a nice grocery store.

We are well on our road trip - loving Oregon so far! The weather has not been co-operating all the time - we had to skip Crater Lake coz the cloud cover was so low and it was so windy that we couldnt see anything from the rim today. We are in Bend and it looks like a lovely place so far! We checked out the High Desert Museum - very nice - and hoping to go to the Newberry Volcanic Monument. But the link for this place doesnt show up any content and I'm not able to figure out if its even open!! Hope to check out more of Bend before heading up north! Thanks again, everyone!

Looks like the website is going through a redesign. But I do believe it closed for the season on October 1.