Keegs,
Not to get too far down the wrong path here, were you thinking the well itself would freeze? I've never heard of that happening. But, I suppose it's possible.
The biggest problem I think comes from the air temp in your basement going below freezing, causing the water line coming in to freeze. It may freeze for some distance towards the well it that goes on for very long.
If I remember your house pic, you have a full basement with no walkout level? That would be the best case for preventing freezing. Do you plan on keeping any heat on in the house over the winter?
For about $30 you can buy a thermostatically controlled electric heater - the 'milkhouse' style with a fan. Set the thermostat so it comes on around 40* and point it at the well line in the basement.
You can also get temperature alert boxes that will place a call to your phone when the temperature falls below a certain point, or the power is out. Of course, you need a landline at the Maine house for this to work which is a downside. Greenhouses and the like use these units. You can also call the box and it will tell you the current temp, low and high temps, and power status.
Perhaps not exactly useful from NJ to ME, but it will give you something to worry about when it calls in the middle of the night - that's when they always call

Dave.