Where are you in Oregon exactly? I suppose I could be in technically "western" Oregon...maybe? Haha I don't know, my horse and I live in Gresham, OR if that's "western Oregon"... We don't have a trailer, but we do live near some really nice trails... And I know of some places to go, like the Columbia Gorge Scenic Area, if you're from around here. That place is really really fun to ride in and it's gorgeous.
ETA- I missed that you said Portland! We're close to Portland, kinda! If you have a trailer, and didn't mind having to pick up Lacey and I, we'd love to be riding buddies with you! :)
Awww, I would love to meet you guys, but I have a vehicle that just barely pulls one horse. I would be chancing it with two. Wish we lived closer, I work in Gresham, about 40 mins away from where I am at now. (Sucky commute!)
I trail ride several times a week with a friend of mine and sometimes my kids. We have actually posted on craigslist looking for new trail riding buddies. I have my own trailer so we could meet you somewhere? I am in Sherwood but we go anywhere especially if it is new to us :)
Definitely try OET (Oregon Equestrian Trails) They often have monthly trail rides and you can join in on any chapters' rides no matter what chapter you join.
There is also a Back Country Horsemen chapter in Oregon, but I don't personally know anything about them.
I'd love to have a trail riding buddy, too. But I don't ever have time to trail ride. =(
Yes, you should come out to Sherwood and go riding with pctrider and I. We go all over the place sometimes up to two hours away for a new exciting trail.
We're a part of the West Valley Chapter of OET and our group is in need of new members. It's pretty cheap to join, there's organized trail rides and playdays, and the biggest perk of all is that you get a GIGANTIC book of all the trails that the OET members submitted; there are hundreds of trail riding possibilities. :)