Mt Jackson is one of the easier fours to climb in summer or winter. It has easy access from the high point of Crawford Notch, is short and moderate. It's a good place to start your winter fours because it offers a quick descent into the woods if the weather is bad. The summit is exposed and can be VERY cold in winter. In the above photo, Jackson is the little white knob in the bottom right.
THE TRAILHEADS
From Crawford it's the ♦Webster-Jackson Trail which is right by the shores of Saco Lake. It's a moderate to easy hike, nice outlooks over the notch at Bugle Cliff. Many do a loop over to Webster using the ♦Webster Cliff Trail.
♦Webster Cliff Trailhead is found further south on RT-302 and is steeper than ♦Webster-Jackson Trail. This also connects Mt Jackson to Mt Pierce and eventually ♦Crawford Path.
THE MOUNTAIN
My first trip to diminutive Jackson was a mid December hike over Jackson and Webster. I enjoyed seeing the little white shrouded rime trees on the summit and took a few pictures. I also discovered what frost bite is all about that day. I've since done it officially in winter on a much warmer day.