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So I've had two kind of completely different experiences moving to mountain towns in the past year. I graduated college and left my home, family and friends back in the midwest to live out my dream of living in the mountains.
Mt Hood
I moved to Hood with a job lined up and housing included, but I had never been there before I moved. Little did I know, I was the only one living there for two months until summer camp started. I worked 40 hours a week in the Windells office and got to go skiing for free every weekend. But once the other 2 people that worked there left at 5, I was the only person on the grounds. I knew literally no one. I don't think I've ever really been that lonely in my life. I was also in the middle of the woods. I would go on solo hikes, but after an encounter with a huge snake on the trail I got a little too freaked out to get too far into the woods alone again. Govy was a 25 minute drive. I would go up and go to this place called the Ratskeller, the bar manager happened to be from Ohio so we bonded and I became a regular. I couldn't really get hammered up there because of the drive down the mountain back. Luckily the spring pass was starting and people were moving in and out. Erica was there for a week so I hung out with her a ton down at the airstrip and we took a trip to the ocean! Reached out to TallT Dan and hung out at the Graveyard for a few weeks with all the boys. Met some other random kid on NS and we would go to the bars and ski, then he headed back to Utah. I was finally making friends, even though they were just for a short time period. My best friend came to visit for a week and then Summer camp finally started and I moved down to the Ark. All the other windells employees got there and the weeks just flew by. Skiing, Hiking, Camping, Beaches, so many adventures with awesome people.
The summer was up and I kind of didn't know what to do with my life. I had 3 days to figure it out, so of course I went to the ocean, went surfing and camping on the beach. Made up my mind talking to my best friends and parents while standing in the pacific. The next day I packed up my car and drove 12 hours straight by myself to Jackson, WY with absolutely no plan.
Jackson, WY
So, I moved to Jackson with a car full of my shit. I had no job, no home, it was kind of a weird time for me. On my way to Oregon I had stopped in Jackson and slept on an NSers couch (Zach) and gone skiing the second to last day of the season. I remember I had thought this place was amazing, I almost didn't want to keep going to Oregon. I sort of stayed in touch with Zach, saying Oregon was awesome like twice. He offered up his couch again. I slept on the couch at his house for 3 weeks. Got a job at a local indian restaurant and an internship with TGR (thanks newschoolers), but came in the middle of a housing crisis. I was making money and still working in the industry, but it was not looking good for a place to live. I remember crying on the back porch one day thinking I was never going to find somewhere to live and that I had seriously fucked up. So after 3 long weeks, sleeping on a couch and living out of a suitcase and my car I lucked into a room in a small little split level with 2 other girls. Rent is $600, which is sooo much, but a really good price for Jackson. So a job and housing, check. Now I had one friend here, Zach. I would go to this local bar and pizza place almost every night (just so I wasn't always sitting on these peoples couch) and made a few friends, mostly the employees haha. Anyways, I moved here in the end of July and it's still really hard meeting people. I miss my friends all the time, like so much, and people here seem to be kind of cliquey. About a month after I moved out I actually started dating Zach (and to think I slept on a couch in his living room for 3 weeks haha). So I've made friends with his friends which has been nice.
Money/Job/Pass
So money is always an issue, at least for me. Plain and simple, it's expensive to live in a mountain town. Between rent, food and trying to keep up a social life, its going to be tight. The best plan is to work for the mountain for your pass (I work like 14 hours a week at a gift shop) and then serve at a restaurant at night to make money for life. Still get 5 days a week to ski, with one full complete day off (other days I can ski till 2).
So for your questions I feel like work is pretty easy to come by, theres always demand, but housing is what's hard to come by (and cheap housing even more so).
I guess each place had their ups and downs.
Hood had a free place to live, small wage, but no friends (until summer camp).
Jackson I had no place to live, no job and one friend.
Both were awesome experiences, but I'm still living in Jackson.
Hey, maybe Bozeman next?