Someone who is thinking of moving here asked about homeschooling in Portland, so I thought I'd share my perspective, limited as it is to the part of town we live in, for the most part, and focused on activities that interest my particular kids.
From what I can tell the homeschooling community is thriving in Portland. There are so many resources and classes and park days that it is really hard to limit your schedule to something that is manageable. I think it can take some time, though, to build a good social network, which has truly been the most important resource of all to us.
For out-of-towners, Portland is divided by a river, and people often tend to look for activities on their side of the river, and there are some (very non-universal) differences between people who wind up on the west side versus those who tend to wind up on the east side. Although this is a gross generalization and many people don't fit this mold, alternative and non-main-stream and sometimes less affluent people often seem to wind up on the east side of town, especially in the urban neighborhoods closer in. The west side has more traditional suburban family-oriented neighborhoods that have less of an "edge," for lack of a better word. East side families are probably more likely to be politically liberal and less structured in their approach to schooling, while west-siders may have a higher proportion of conservative and religiously-based homeschoolers. The homeschooling moms I've met have been pretty universally really wonderful people, whether conservative Christian or unschooling Pagans, so no judgement are meant by these generalizations! My impression is also that the west-side moms may be a bit better organized than the east-side moms, as evidenced by some very long-standing and well-attended events (like Cook Park park day) and a wonderful homeschooling resource center,
Village Home. However, more and more organized activities are occuring in and around east Portland, and Village Home is looking for an east-side location and hopes to open up classes in inner-east Portland next fall.
Beyond Village Home, the offerings are rather amazing: classes of all kinds at many community centers around town, fencing, swim team, archery, aikido, OMSI science classes, ice skating, roller skating, rock-climbing, girl scouts, campfire, and much more all have day-time classes/times especially for homeschoolers. Also, one-time or periodic field trips are often arranged, like train trips to Seattle and a tour of the Tall Ships. People frequently post information on smaller classes or events they are offering, such as cooking classes, scrapbooking, dragonology, hikes, and game days. Last summer there were at least four different homeschool park days in different parts of town. One of these routinely had 40-60 people show up, as I understand it, and the one I attend probably had 25-40 people every week last summer.
All that said, I think it can take some time to find your way to the families that will be your main social support system. It is tricky to find a family where the moms hit it off, the kids hit it off, you live in reasonable proximity to each other, and your schedules mesh well. It also appears to me that there isn't an overabundance of teenaged homeschoolers, at least on the east side. Our local homeschooling organization has begun sponsoring several dances each year, and by all acounts these are really fun, so hopefully that will help teenagers find like-minded friends.
Anyway, others feel free to correct or add to my impressions. I think it would be entirely possible to find like-minded homeschoolers in whatever area you wound up living in Portland, and it would be extremely easy to fill up your week with activities. And most of all, I've just found so many really, really nice people among Portland homeschoolers. I just wish I had more time to invest in more of these friendships!