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I can do the Killington Skyeship to Danbury CT in just over 3 hours. Tough to do, figure an average of 65mph on the VT state roads and through Springfield, Hartford, Waterbury and 75mph on the non-city parts of the interstates.
I haven't daytripped Killington on a weekend morning in a looooong time but if I did I bet I could get it down to under 3 hours leaving the house at 5am on a Sunday.