I live sort of the area previous poster is talking about - western howard county/frederick/lower carroll county area (in Mt airy, they all meet, but that area is farm area with 30 minute to drive to Frederick and Columbia, 1 hr to DC and Baltimore.) Carroll County has some good schools, at least rating wise. If you are considering public schools, that is. Carroll county is cheaper. I personally would love to move to the beaches of DE all year around, but that is just me. I think there are more alternative schools in Howard and Frederick counties, and Montgomery counties (howard and montgomery probably being more expensive areas to live, and then frederick the last on that list) Part of the reason for less hippyish then west coast is probably our proximity to DC, politicians and government businesses are the norm here. Many people work for government contractors, there are a few military bases, it is typical to meet someone who has government clearance or works for a government contractor or works as a government employee, at least within the 1 hr commute of DC and Baltimore
As to the weather...well, it still gets cold here. My sister lives in NJ, so not as cold as that, but still we have blizzards, but a month later can have 70 degrees. We tend to get bad weather in February and March. I don't know anything about OR weather. Typical summers could be like 80-90 degrees (could be higher, we have had temps over 100+) with lots of southern humidity, and winters can be cold with nor'easters. So we get the best of both, LOL. Most people can't drive in the snow because we don't get a lot (unless you move to western MD, and then it is like 100 average snow in winter) so we get some winters like this winter, where it is just grey all the time and cold (10-30s), but hardly any snow - I don't think we have any measurable snow yet, but then a few winters ago we had 2 blizzards back to back and like 25 inches of snow (Sorry to rattle on about winters - I am so ready for spring here)
I too would say overall conservative with some few spots mixed in. For instance, I want to send my daughter to the Lucy School in Middletown, md, an arts based school. However, eh, the area, Frederick, Middletown (I grew up in that area) not so much a place I would want to live, they have artsy community downtown, they have some hippyish stuff, but overall conservative. There are groups for alternative parenting, there are different schools, but I don't think there are any hippy type places to live.
I hope that helps!