Portland to Deschutes/The Dalles is 100 miles. Riding it in one day is 
totally doable, but maybe less than the amount of fun most people are 
looking for at the start of a 360 miles (mostly) off-road odyssey. Two days 
should be pretty pleasant but perhaps not amenable to as many people's 
schedule?

If you fall in the latter group, Portland SagWagon 
<http://www.portlandsagwagon.com/Site/Blog/Entries/2014/3/1_Oregon_Outback.html>
 
can shuttle you from Portland to Deschutes SP in about 2 hours 
door-to-door. I'll also mention Deschutes SP is a beautiful camp site to 
start (or finish) any ride. Taking a late shuttle would allow one to spend 
a day sight-seeing in Portland (always recommended), camp at the Deschutes, 
and then start one's Oregon Outback adventure bright and, if not early, at 
least fresh the next morning.

Full disclosure: I operate said Portland SagWagon. :)

Cheers,
-Allan

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