Amtrak First Timer on the Adirondack to Montreal

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Your best bet would probably be taking the Lake Champlain Ferry out of Port Kent. The ferry between Burlington and Port Kent operates daily through September 29th, after which Amtrak will no longer stop at the station until next May. Starting today the ferry leaves Port Kent at 3pm and 5:30pm, so if the northbound Adirondack is on time (and the likelihood of that is very slim) you could catch the 3pm ferry, alternately you'd have to wait until the 5:30pm ferry which is the last one of the day. Foliage tends to be near peak or peak the last weekend of September in northern Vermont and New York. If you do take the ferry, you would get on the southbound Vermonter in Essex Junction the next morning, about 20 minutes from downtown Burlington and accessible by bus. There are a few hotels within walking distance from the ferry dock in downtown, but not much closer to the train station is Essex Junction. There is also an abundance of great restaurants in downtown Burlington, especially on Church Street, a pedestrian marketplace with a bunch of local shops, restaurants and even a shopping mall.

There is also a ferry out of Plattsburgh that runs year round, however you would not have an easy time getting to an Amtrak stop in Vermont. That ferry runs to Grand Isle, VT, where you'd have to take a cab (if there even is one in that area) to Burlington or St. Albans.
 
My wife and I took this trip back in June. My observations:

At the border going in either direction, neither of us had problems. I noticed that essentially the customs agents do a first time sweep of all the passengers. Sometimes somebody is asked to bring all of their luggage to the lounge car. Usually this happens the first time through but the agents did come back at least once to ask somebody else to bring their luggage to the lounge. I'm sure some of them get picked at random. The biggest difference between 2013 and my last trip in July 2001 was no dogs were brought through the car sniffing out drugs.

In Montreal, we arrived and went up the escalators and had to find our way out. Of course station personnel were around to guide people. However Central Station is a part of the greater Underground City, so there's lots of people passing through who have no train business.

On the way home, we arrived at Central Station and got in line. A porter came up and down the line asking if anyone was interested in having their luggage taken for them. I wasn't going to do it until I heard him say "the escalator is out of order". We had large suitcases, so I opted for the porter. He took our luggage and us and we found a seat on the train, several minutes before the rest of the crowd were let through.
 
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