I have quite a bit of vacation time saved up, and was thinking of taking two weeks just to explore the state of Wyoming. What I'm really interested in is avoiding the touristy areas (although, I do want to hit up Yellowstone in maybe another trip), and exploring some of the small towns. My first question is, has anybody here done that before?
My first visit took us first to Evanston for our first night in Wyoming. It seemed like a perfectly ordinary city, unremarkable. We then stopped in Green River, saw some sights, but did not spend the time to see the Flaming River, which is supposed to be quite the sight. From there to Rawlins was boring desert. We were not interested in Laramie or Cheyenne, so we turned north to Casper. Over the next few days, we stopped in Douglas, Lusk (small town and WINDY), Newcastle, Sundance, Moorcroft, Hulett, Gillette, Buffalo, and then Yellowstone. It was a great trip, and we eventually decided on Hulett.
I suggest stopping at the real estate offices in the towns and have a chat with the people there. They know their towns and areas very well and can be a fun visit even if you are just playing tourist. You can tell them you are just playing with the idea.
I would, of course, be trying to get a taste of the place to determine whether it is where I want to steer my life. Am I setting myself up for boredom, or is this really a good idea? If so, can you suggest a starting point?
I think it is a fine idea. In general, everything I have seen in the southern half of Wyoming is desolate wasteland (except around Yellowstone). It makes Nevada seem interesting. The south-west is next to Utah and is heavily Mormon. The north-west is beautiful, but probably not affordable because of all the rich people and the park land. The northern third of Wyoming is great scenery.
Towns I would recommend for a visit would include Green River, Newcastle, Upton, Sundance, Moorcroft, Hulett, Pine Haven, Buffalo, Ten Sleep (very small but scenic), Thermopolis, and Cody. There are quite a few places I have not visited and maybe others can suggest them, like Sheridan, Pinedale, Riverton, and Wheatland for example. Again, real estate agents might be able to point out the interesting things to see and do.
Good luck!