The Cog Railroad (above)
My brother and I planned this trip a few months in advance and decided that we wanted to do a big loop, taking two different trails, in order to experience as much of the mountain as possible over a 3 day weekend. We decided to take the Ammonoosuc Ravine trail combined with the Crawford Path for the ascent, followed by the Gulfside trail and the Jewell trail for the Descent.
The Ammonoosuc Ravine trail had a few major advantages. There is a large parking lot for hikers at the cog rail station, the trail begins approximately 500 ft higher in elevation than the trails on the other side of the mountain, there are numerous waterfalls, and the lake of the clouds. Though there are a lot of advantages to taking this trail it should be noted that the trail is very steep in spots and usually wet. In my research it was rated as one of the more difficult climbs, but in my opinion that made it all that more rewarding.