I spent a week in Gardiner a couple winters ago. Drive times are about dead on for Big Sky and Bridger, but most people we hung out with spent all they're time in the backcountry. It's a small town, so you won't have trouble meeting people. We stuck out like sore thumbs while we were there. Fortunately we had a local guiding us around.
There's definitely no shortage of things to do. Winter camping, BC skiing, hiking. It's secluded enough that you can get lost (in a good way) pretty quick. The guy we were staying with lived in a Tee Pee just outside Gardiner for almost a year with no problems. It was amazing, it was only a 20 minute hike from the road, yet he said he never once came across another person out there (that he didn't invite at least). You've also got the Yellowstone entrance at the end of town. In the winter it's dead, and the boiling river is about an mile in, so you can go have a soak after a long day.
There's definitely a redneck sorta vibe, but all the people we met were kind and gracious. If you do move there, make sure you're stocked up on long underwear, it gets damn cold there.
Remind me. We'll send him a red cap and a Speedo.
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