Hi Shannon! Welcome from over in Windsor County! I live just south of Woodstock, and west of Ascutney.
Have you lived in the north country before? What kind of vehicle do you drive?
The winter is hell on driveways and cars, but not as bad as mud season. On gravel roads, it's not uncommon to see ruts in the mud that are over a foot deep. It's very hard to get through. (The surface of the road thaws, and spring runoff saturates it. But below the surface the road is frozen, so the water can't drain. It's a nightmare.) In the winter your grass driveway should be frozen, but when it thaws (as it does periodically during the winter) that's bad.
Sorry to be the bearer of bad news! I think you should definitely have some gravel dropped in that culvert area, by someone who knows what they are doing. Ask around; there are guys with dump trucks and gravel, and then there are guys who really know what they are doing.
I drove a Chevy Volt (plug-in hybrid) when I moved to Vermont. The first winter sent me off to the dealership to buy a 4-wheel drive. I hate having a vehicle that uses only gas, but I couldn't manage the roads with the Volt, which is extremely low to the ground.
I think the fire department question is important, but less so in Vermont than in some other places. Keep in mind as you look at your land that we have had precious little rain this year, so things are much drier now than usual.
And hello! Welcome!