There are guys in the area who plow based on seasonal contracts. You pay at the beginning of the season, and if it snows, they come and plow whether you are there or not. The trick is getting someone who is good at plowing a gravel drive, so that your driveway doesn't end up in 4 or 5 piles when the piles of plowed snow melt at the end of the season. Then you need the guy who does driveway grading and may or may not be the same person who does the winter snow plowing.

While the area is rural, there has been a city population (weekenders, retirees, landed gentry) since the early 1900's and so there are longstanding services and traditional ways of getting things done.

Back in the day, the train from the city came right into town. At some point, the tracks got pulled up (we looked at a house built in 1933 that used rails from that line as the floor joists - like a rock that house was) all the way back to Wassaic NY, where you can still catch a MetroNorth train back to the city. Currently, the segment from Wassaic to Millerton is paved as a rail trail for cycling, and eventually the plan is to run the trail all the way up to Chatham NY - 46 miles.

Anyway, a lot of history and interconnectedness with NYC. A very nice lady I spoke to at one of the local eateries remembered as a girl watching all the dairy farmers bringing their milk to the trains to take it down to NYC in the morning. If you look on Google Earth, you can still see the old rail lines crisscrossing the entire county.