I live in Portland, OR. It is really beautiful and amazingly family friendly - but the winter season is rainy.
There are tons of hikes, parks, mountains - skiing on Mt Hood, Mt St Helens Volcano. For kids there are lots of attractions - OMSI is one of the best kids museums in the US.
The Oregon Coast is also beautiful - but the water is cold year round.
Kosher cholov yisroel Pizza store at the J. Safeway and Albertsons have fleishig delis (Safeway has Sushi) under Oregon Kosher which is run by Rabbi Tzvi Fischer of the Portland Kollel.
If you want specific info PM me.