Greetings!
Webster Cliff Trail begins on the east side of Rt 302, across from a plowed parking area on the side of Willey House Station Road. It is part of the Appalachian Trail and it is blazed in white. Ascending, you will likely want snowshoes. This is a good time of year to hike this trail, as there are no people, manageable snow cover, and it is a great trail for working those quads! There is a missing sign at the junction with Saco River Trail, but you will easily see that the blazes for SRT are blue. The Saco Lake Trail sign is intact. There are two blowdowns in the first mile. They fell during a storm at the end of October and I haven't yet removed them (I was cleaning waterbars and didn't have a large enough bowsaw with me). They are easy enough to avoid and they may not be entirely visible under the new snow.
The trail is easy to follow, freshly blazed, and has a great view from the top of the open ledges. If the top of the open ledges are icy, you will want to switch to crampons for traversing over to Mt. Webster. An ice axe may be warranted. The trail winds its way over to Mt. Webster, ascending many rock outcrops along the way. There, on Mt. Webster, you will likely encounter a trail that has been broken in by other hikers on the more popular route (Webster-Jackson Trail, Webster-Jackson Trail-Jackson Branch, Webster Cliff Trail, Webster-Jackson Trail-Webster Branch, Webster-Jackson Trail). You can descend the Webster Branch of the Webster-Jackson Trail here. Peakbaggers will want to continue on the Webster Cliff Trail to Mt. Jackson, but Webster is just as nice, view-wise. You could continue on Webster Cliff Trail all the way over the boggy territory to Mizpah Hut and descend back to Crawford Notch via Mizpah Cutoff and Crawford Path. Or you can continue all the way to where the Webster Cliff Trail ends- just north of the summit of Mt. Pierce, where it meets the Crawford Path.
I have hiked this trail in winter, and I found it to be a lot of fun. If I, (an overweight old woman), can do it, pretty much anyone with some winter gear and hiking experience can.