Buying a Subaru? Might as well buy new with the absolutely ludicrous prices people want for used ones. That's about the only car I suggest buying new, other than Mini Coopers for the same reason. If you go with a different brand, and don't mind used, you can get way more for your money, even if it doesn't have as much street cred in insert random mountain town name here.
I had a tough time deciding what to do when I moved here last May, as my main car (2005 CTS-V) is not exactly optimal for Montana winters or off-roading in the slightest. However, I LOVE it, and the thought of trading her in for a car that would cost nearly TRIPLE what I could get for trade-in, and not nearly as fun, fast, or luxurious made me decide against buying a Subaru.
I instead went with a used Chevy Trailblazer 4x4. Decked out, leather, sunroof, and not a scratch inside or out. It looked like it rolled off the showroom floor and had super low miles. My price? A bit over 10 grand because their resale is horrid. I know it's not going to be nearly as reliable as a Subaru in the long run, BUT it's been fantastic for my purposes, which sound like yours. First thing I did was put some great tires on it, so going to trailheads via nasty rough roads up steep and rocky mountains has been no problem. Given, I usually have to pull to the side so the Jeeps can pass me by. Haha. I put snow tires on it for the winter, and it was unstoppable to get from my driveway to the main road, no matter how deep the snow got. Never bothered shoveling or plowing a path. This thing just bulldozed it's way through the snow like I was on pavement. It's been absolutely great for all my outdoor activities. The downsides? Crappy SUV handling, crappy SUV gas mileage, questionable quality. The upsides? Good off-road capability (selectable 4Hi, 4Lo, and 2Hi, and an optional G80 locking diff) with tons of ways to upgrade, tons of cargo space, superb in deep snow, plenty of power, and the best part? I get to have TWO great vehicles for less than the price of a very used Subaru!
For a car quiver of one, I still think Subaru's the way to go. But you can save a lot of money buy going with another brand. Another thing to consider are the new Jeeps. Yeah, their gas mileage and quality used to be pretty bad, but they've come a LONG way in their latest iterations. Their quality is way, way up, and the new Pentastar V-6 their putting in the Wrangler and the Cherokee is a phenomenal motor. The Cherokee gets decent gas mileage (23 mpg with 4WD), with the Wrangler getting 21. I got a chance to drive a Dodge with this engine, and it is VERY smooth, with admirable power, and every review I've read is expecting these things to be very reliable due to some new, but simplified technology. Don't rule them out if you can swing a good deal.
Edited by AustinFromSA - 3/15/12 at 4:47pm