5. The Adirondack, New York to Montreal
Assuming you don't need to be at Club Supersexe for your buddy's bachelor party, like, today
, hop the only East Coast route to crack the list and meander up the Hudson River past West Point, an abandoned island castle that once served as an arsenal, and Lake Champlain, before rolling into Montreal for an epic weekend of poutine and Labatts.
Fares from around $65 each way. Bargain! Leave in the morning and pull into Montreal just after happy hour.