travel and rhum

I did my first winter hike last year, which was Monadnock. I'm looking to do many more this year and I'm looking for suggestions on which to do.

I'm roughly a 3-4 hour drive away so I'm going to go up there next weekend and sleep in my vehicle. With the days being as short as they are, I'm looking for suggestions on which 4,000 footers to entertain.

My big thing is that I know some of the trailheads are on roads that aren't maintained during the winter, which can add quite a bit of length onto the hike.

My question is, what 4,000 footers would you suggestion that don't have miles long treks in before getting to the trailhead?

I'm new to winter hiking as a whole, so I want to get experience while being as safe as possible.

As the title states I'm looking for some wider/baggier pants for hiking, most all of them are slim fitting tech pants that don't fit me very well. Any recommendations would be appreciated!