Light AT tech gear is my preference. You will be thankful on the ascent. Taking skins on and off can be tedious but the trick is, don't be in a hurry. As far as Greylock goes, have not thunderbolted in awhile but being lower elevation you really need to pick your day. This year I don't think we will see good conditions until late in the season though. However last year, even with the great snow things were pretty dangerous until spring.
Don't ski the trees, ski the spaces between the trees.
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