Join Date: Aug 2006
Location: western Washington
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A few decades after the invention of the derailleur, the Eugene Parks Department took a busload of folks and bicycles up to Crater Lake to ride Rim Drive. Let us out at Rim Village and we rode clockwise, the best way to see the lake. Only problem with that is that the last few miles are all uphill. But, after a day of riding up, down, up, down, etc. it really wasn't that bad. Elevation is a bit high, so don't plan on going really fast unless you're acclimated.
The boat ride leaves from the Cleetwood Cove Trail at the NE side of the lake. You hike down to the water, ride the boat, and then have to hike back up. I would say, do the boat ride first, drive around the lake, get prepared for what the ride will be like.
Diamond Lake is a good place to stay. Cabins there have kitchens, there's a store where you can get food. If you really like to ride your bike downhill, there is a long descent down the North Umpqua highway (20 or so miles after you leave the top) going west from Diamond Lake toward Roseburg. Maybe you can ride and your spouse can come along later.
Diamond Lake used to have great fishing, but was taken over by some little introduced bait fish that eats all of the little rainbow trout. Ashland, yes.
So: Drive over the Cascades to Yakima. Drive south on 97 through Bend. Look at the High Desert Museum just south of Bend. For a mini-crater experience, drive up the twisty road to Paulina Lake (used to have platform tents, and cabins, to rent there). Go on to Ashland, see a play or two. Go on to Diamond Lake. Drive the rim, do the boat trip. Ride the rim, celebrate. Drive down to Roseburg, and then up I-5 to Pugetopolis, or west from Roseburg to Coos Bay and up the Oregon Coast.