I love to travel, but I always enter a black hole of self-doubt beforehand that turns me into Emma Woodhouse's father. Why am I leaving home at one of the prettiest times of year? Why subject myself to the stress and the complications? Why not sit in the dappled shade of my garden and be happy that I have a brief respite? Is it not true, as
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Not northeastern, but likely to meet most of your criteria anyway: Ashland, Oregon.
Location: a stone's throw from the California border just off I-5, next to the Cascade/Siskiyou foothills. There are definitely Seasons -- August can get close to Arizona levels of warm, while winter (usually) brings snow and visiting skiers for nearby Mt. Ashland, but the average climate is less extreme than either the Southwest or the upper Northeast. Population runs 15,000-20,000 depending on the time of year.
Culture: Two institutions dominate the community: Southern Oregon University and the Oregon Shakespeare Festival. SOU has grown considerably in the last couple of decades, partially but not entirely due to OSF's growing national profile. OSF -- as you may in fact know -- is one of the premier regional repertory theaters in North America, with three theaters, a ten-month season of 11 different plays plus a *lot* of side events, and an increasingly ambitious focus balancing Shakespeare and other classic material with newly commissioned work. Alongside OSF, a lot of secondary theater and music companies have sprung up, and there is a long-lived jazz festival based in nearby Jacksonville.
Balancing the arts-and-culture community is Jackson County's long-standing (and sometimes teetering) agricultural and timber economy, so there are in fact barns and farm properties in the immediate vicinity. Mail-order fruit pioneer Harry & David is headquartered nearby, complete with legendary pear orchards. The real estate market is...interesting, as there's tension between the tourist/retirement shoppers (so there are some decidedly spendy properties out there) and the average-townie/local market (who are looking for much cheaper options).
My experience with Ashland is as a long-term tourist -- I've been spending a long weekend or so per year there for several decades now, inhaling five plays in three days with a succession of tour groups and staying in a great variety of facilities (from the college dorms as a teen to the signature historic-landmark hotel next to the OSF campus). If I ever hit the Powerball jackpot, however, I will start my hunt for a nice little downtown Ashland condo within the week.
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