If you are anywhere close to Portland, my suggestion is to give the Portland Wheelmen Touring Club a look - including trying a weekend ride or two.

This gives a chance to meet fellow cyclists including potentially some with experience touring in the area and potentially even others who might be interested in touring with others. In addition, you can get more information on their Columbia Gorge Explorer ride over Memorial Day weekend - which is a four day self-supported touring ride done with the group.

There are pro/con on touring by yourself or touring with others and often this ends up being a preference thing - and no single "right" answer. However, one of the choices might be doing some rides with other like-minded cyclists.