Hi Mohamed, (hiked w/ you on the Osceolas)
I was on Ascutney yesterday. It is a small mountain, but I am always surprised at how rough the footing can be. Toe Cozy and I went up the 'cold' side of the mountain on Brownsville trail. There is a quarry early on and we decided upon crampons at that time. It could be considered overkill, but there is a thick layer of ice under a thin layer of snow and we just didn't want to chance a bad fall. There are lots of rocks and roots on all of the Ascutney trails. We went down the Weathersfield trail, which was definitely the 'warm' side of the mountain with much less snow or ice.
Here's how I see it:
Windsor trail: the most steep and shortest - challenging - a pretty stream comes down off the mountain that you follow for a short while (approx 2.7 to summit) - probably still snowy and icy
Brownsville trail: Interesting with the quarry and ice falls/formations (approx. 3.2 to summit) - probably still snowy and icy (on the upper mountain we lost this trail and ended up on the Windsor trail)
Future's trail: longer and more gentle, pretty, follows close to the mtn road at times (approx 4.6 to summit) - not sure of ice and snow
Weathersfield trail: probably the most popular - for good reason. Not too difficult, passes waterfalls and a beautiful stream. We saw people from the Dartmouth Outing Club on this trail doing a beginner ice climbing course. Little snow by now, but a few icy spots. (approx 3.4 to summit) This would be my suggestion.
Hope you have a great hike and that the weather holds up!
Hanna