We've done New York City to the Canadian side of Niagra Falls and we've done Connecticut to Virginia, but the longest feeling trip was when we took what should have been a 2hour trip from New York City to Ct in a blizzard and it took us 10 hours. Our car finally got stuck around the corner from our house and my husband never made it to work anyway. that certainly qualifies as one of the top five stupidest things I've ever done. I was never so greatful that I had children who never got bored!