I know a little bit about the area now, having gone around wyoming and montana and idaho last year looking for a place (south dakota too, come to think of it, too close to Minnesocialist though.)
If you come here in Winter, this whole area, do yourself a favor, bring warm clothes, and stop by a Walmart and get you some car tire chains (those web looking things) or get studded snow tires. You will not get out of any driveway that isn't inclined downhill otherwise, and you won't get into those driveways without a speedy head start to begin with. Snow... if you go up past Snowdance (the map calls it Sundance) expect mounds of 4 foot ice and snow up until Late March Early April. We drove through last March and it scared the poop out of us since our little 1 foot clearance car kept bottoming out in the ice pits in the middle of the roads just off the highway. The highways are well plowed, and Mama Liberty's place, if you stop by there, is in a gorgeous area.
Wind River Canyon is just downright sexy (and there's no cell signal in the canyon, yay!) but there appears to be huge meth production and the accordant law enforcement psychosis down in Lander. Guess the natives are stuffing all sorts of NEW things in their peace pipes down on that reservation, eh? Saw more keystone kars there than anywhere else in the state, even in BIG cities (Lander's probably the size of Newcastle, but they have a LOT of kop kars.)
Speaking of Idaho, as soon as you pass through the Teton pass (After going through Jackson which feels like any coastal college town where nobody's paying attention to where they're going and cross the road without even looking first), Idaho itself seems to be a lot more like Delaware at higher altitude... also LOTS and LOTS of latinos but most of the ones I chatted up seemed the hard working "been here since the times before Guadalupe Hidalgo" types, but that was just my opinion. Montana is fun, the rents are higher and it gets even more pipe breakingly cold up that way. They produce lumber on top of energy and such. They also have more ticks, and wolves, i'm told.
Just remember, there's all sorts of things that can eat you in the northwest, bring a skinning knife and a gun, and if you don't, that's when you'll probably run into something ugly, remember, preparation somehow always prevents having to do what you prepared for. If you come unarmed, since you are "new yawkaz" and all, don't get stuck in the snow. They do plow here in the nortwest quite well. The side roads not so much but the main thoroughfares in towns and the highways were clear from the dakotas to Idaho when my family came lookin'. If you got one, bring a CB or VHF or a ham rig that can hit those frequencies.
If you stop by Mama Liberty's for awhile, I'll be glad to come down and break bread with you. (She makes some awesome bread, and her tap water is as delicious as she claims.) It is a wee bit of a drive, and if you do it in the winter, want to know a week or so in advance.
Enough gushing. As for road trippin' in the winter, here's my take:
If you drive, my strongest advice is to stay clear of Chicago (go through the mid southern rural area instead) and be EXTRA leery in Indiana. It isn't Lincoln's Childhood Home as it says on the placards, for nothing. Been through a few times and saw tons of people being arrested or pulled over each time. I usually try to have a full tank for the Ohio and Indiana runs so as to never have to stop and to be able to use back roads. I can give you some fairly clear routes to run on the roads, but my bet is to head through Illinois, west to Iowa, cut straight north to Minnesota and then straight west until Rapid City, SD, from there, you can cut west north of Rapid, through Sundance, Wyoming, which is right off the interstate (I 90) and head south to ML's in Newcastle, or cut straight past Mount Rushmore from Rapid and after some winding windy roads which take two hours to cross 50 miles or so, you'll be right at her front door (more or less.) Crook county, by the way, is possibly the prettiest area short of going up to Cody/Sheridan/Buffalo up in the Big Horns or all the way to the Rockies.
If you take the southern Nebraska route to ML's you'll be coming up through Lusk, instead and heading north through some pretty desolate area reminiscent of post apocalyptic videogames and movies. Not quite Mad Max, but possibly Borderlands without the axe wielding cannibal Psychos. Just coyotes and truck scales, mostly, oh, and wind... and those thrice damned antelope. Try NOT to drive at night if you can, and if you do, give yourself time, go slow and expect stupid four legged grass eaters of all sorts to try jumping in front of whatever you drive. Them's good eatin' if you shoot them instead of ramming them. Expensive game meat if you trade body work and engine work for a few dozen pounds of meat..
Oh, and the best part about Wyoming and Montana? #1 and #2 states for being least likely to get a traffic ticket, period. So if you got a broken headlight or tail light, don't fret, look around you, most people, possibly even the cops (as few as they are) probably have two.
