If you weren't a former racer I would invite you to our club rider tomorrow morning. Awesome little 27 miler to start the day.
If you weren't a former racer, I would invite you to join me and a couple of buddies Sat. at 2:00.
You should check out the local stores like Veloce, West End Bikes and Western Bike Works to see if they have any "store rides". Most do.
I hear Rapha has local team you might be able to ride with. I heard last Sunday they rode a 120 miler, with several thousand feet of climbing.
Also check out the Portland Velo. They have great rides at all levels on Sat. mornings. Hammer-heads Included. They run it like a boot camp, but it still pretty fun.