Never having been to Oregon, what can I expect on this drive? I hear it's pretty. I also here it's a bit boring. Any recommended stops while on the way? How long will it take? Other tidbits of info appreciated. Thx.

Assuming this is a summer trip, go on the route over Mt.Hood, through Government Pass and take the turn off to Timberline Lodge. Spend about an hour watching the movie about the building of the lodge and exploring it, taking a trail, taking photos. Then continue on your way. At the Warm Springs Indian Reservation, stop at the museum. I forget the name. It is wonderful. Then on down the road. The rest of the trip is through the high desert and it is interesting country but maybe gets boring to some.
The trip is 4 hours without stops.

I agree with the previous poster; stop at timberline lodge if you have the time and take that route to bend- its beautiful and you wont be sorry; esp in the summer- the wildflowers are amazing

If all your driving makes you a little hungry, you can stop in Madras at Original Burger Works - they have great Marionberry milkshakes! As you enter Madras the road will split the restaurant will be on your right not too far into town. By the way, you'll love Bend! We are headed there next week!

An alternative route is to take I-5 south to Salem (boring unless you stop at the Woodburn Outlet Mall), then head east on Highway 22. I really enjoy this drive, which starts out in rolling farmland, then heads up over the Cascades running parallel to the Santiam River. Stop in Detroit (just above the reservoir) for a bite to eat, and in Sisters, a cute little western town, for some more shopping. Along the way you'll have spectacular views of Mt. Jefferson, Mt. Washington, Three-Fingered Jack, and the Three Sisters.

If you've got lots of time, follow the sign to Camp Sherman (eastern foot of Cascades), stopping for the short walk to the head of the Metolius River. This is a place postcards are made of. Spend a half-hour poking around Camp Sherman's general store, then go the extra few miles to the fish hatchery. Sounds dull, but it's actually interesting and kinda fun. And the Metolius running through it is awe-inspiring gorgeous.

Other places worth a stop are the marina at Suttle Lake (great brick oven pizza at the restaurant here), and Black Butte Ranch, one of my favorite vacation spots on the entire planet.

The drive non-stop is about 3.5 hours, but you can easily make a week or two of it.

Oh Beachbum, I want to weep reading your wonderful description of my favorite part of the country, while I sweat in SW FL. Even if you take the Timberline Lodge rte. Richard1, try to make an excursion to the Camp Sherman, Suttle Lake, Black Butte Ranch, Sisters area while you are in Bend. Enjoy Central OR!!

I second beachbum's route. I will say I am biased but it is such a beautiful drive through my home territory. I actually haven't ever gone through Detroit because I take Hwy 20 (the pass just south, that joins with the Detroit pass in the mountains). Camp Sherman is fun, Sisters is cute (some say touristy and it is but still fun).

Portland people tend to go over Mt. Hood, which is pretty but Madras and environs are not so pretty to me (I love Oregon but not central oregon desert). Give me the green and the mountains for longer. If you are doing a roundtrip maybe take both.....

Outside Bend is a nice High Desert Museum (say hi to Spike the porcupine).

Like Sara, I too have an obvious bias. But if you do go over Mt. Hood and are interested at all in rock climbing, stop at Smith Rocks, a few miles off 97 to the east and just north of Redmond. Maybe you'll see someone trying to scale Monkey Face.