NYC is pretty safe, less crime than Chicago or DC. Just be sensible, as in any large city--don't carry too much cash, don't keep it in your back pocket, etc. And Penn Station is chock full of police and National Guard since 911, as noted. You can overnight nearby--ask others here where--or we like Ramada Eastside, fairly inexpensive renovated apartment hotel on Lexington Av and E 30th St, nicer cleaner Murray Hill residential neighborhood. It's a taxi ride away from Penn Station. But others can tell you places closer.

Or you of course can also go only as far east on the Lakeshore Ltd as Albany, NY, and overnight there, staying in that downtown hotel, the Crowne Plaza. The hotel used to do a free shuttle to the train station, or you can take a taxi. You can see the Empire State Plaza, with its museum, and the State Capitol, and walk from Pearl St on that new walkway by the Hudson River. You can also see the old Albany train station, at least from the outside. Then you could catch the Adirondack north the next morning. I think kids would like NYC more, you could perhaps do both--go to NYC, overnight or two there, then Adirondack, 3 nites at least in Montreal (first is when you arrive latish), then back S to Albany only, overnight, then W on Lakeshore back to CHicago. Or you could come home via Windsor and Detroit, as someone suggested. You could take Viarail between Montreal and Quebec City too, and come back to Windsor from Quebec City--it's truly gorgeous, fascinating, exotic, lots to do and see, and again, fabulous food.

I do not recommend that you get off the Lakeshore Ltd and overnight in Schenectady, though that's the closest stop where the Lakeshore Ltd and Adirondack both stop. But there's little to see there, and the station is dumpy . . .

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When my daughters were 10 and 9, we rode Texas Eagle to Chicago, and connected w/Capitol Limited to DC, then a short hop to NJ on a local (for a two-day visit), then on to NYC for four days. We returned to Texas via the Crescent (NYC-N'alwns) and the Sunset Ltd (NO-Houston).

My kids say a large, fun part of the vacation always has been the actual train trip. Of course I agree. We have combined rail and air segments when time is short.

If time is long, one option would be going to Chicago, taking the California Zephyr to NoCal, then the Coast Starlight to Seattle, then the Builder back home. San Fran is great, and so is Seattle. Sacramento has the Cal St. RR Museum.

The CZ, Starlight and Eastbound Builder all offer great scenery.

Eastbound? Boston is a great destination -- albeit the home of the BoTox -- via the Lake Shore Ltd. We've done that, too.

Hope this helps.

Have you considered making New York your final destination? It's crowded and noisy, yes. But finding a "reasonably" priced hotel (by New York standards) isn't totally impossible. And the place has enough kid-friendly attractions to last a lifetime.

Boston, which is much smaller and "quainter" and far less hectic, is another good choice (take the Lake Shore Limited from Chicago). And I second the suggestion about taking the California Zephyr from Chicago to San Francisco.

As for Montreal. . . parts of the city are pretty. But unless you plan to spend most of your time wandering through the shops in the huge underground mall, there really isn't much to do. Frankly, your kids might get bored very quickly.

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Originally posted by joefamily:
You could go through Detroit then bus to Windsor and take Via on to Montreal.

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How hard is this to do? Is the bus an Amtrak or Via offering? Would we need to cab it from the Detroit station to the bus and from the bus to the Windsor station? I've never been on the Via and would dearly like to.

And here's a related question: What's the Detroit Amtrak depot like? I was in the Detroit Greyhound depot 25 years ago (how time flies) and the Detroit airport 5 years ago, and neither had much to recommend it. I'm not looking for fancy shops. My wishes are a safe place to wait, a chair to sit in, and a functioning restroom.

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I second the recommendation of the circle trip - California Zephyr to Coast Starlight & return via Empire Builder. I would not do it in the reverse direction - best chances for daylight scenery in the clockwise direction.

I also heartily concour with the description of the Schenectady Amtrak station - what a dump! Keep in mind that the LSL has a poor on-time performance coming from Chicago east, when considering connections. If you haven't been to Boston - consider that for sightseeing for your children. Lots of historical stuff to do there.

One of my favorite destinations has been Whitefish. Very much a destination vacation town with lots to do. Beautiful depot. At least 2 car rental companies (Hertz and Budget) will have your car ready at the depot. Motels are pricey in summer. I usually stay at "The Cheap Sleep", actually an excellent cheap no-frills motel.

You could do a loop up with the Adirondack, overnight in NYC or perhaps just Albany, go up the Adirondack, overnight in Montreal, continue next morning on Viarail to Quebec City (it's just 3 hours or so on Viarail), and return on Viarail to Toronto or Windsor, then back thru Michigan or maybe Buffalo . . .

You know, there is also that Blue Lake train from Chicago to Port Huron (the one that used to go to Toronto). Port Huron is in the Blue Lake summer resort area on Lake Huron in Michigan. I wonder if you can overnight there and then catch a taxi easily across the border to Sarnia, ON, where Viarail has some kind of train that connects to Toronto, I think. Or do that in reverse, get to Sarnia, taxi to Port Huron, overnight there and take early train back to Chicago. I cannot imagine the taxi would cost a lot; it's very close by. Of course, with any border crossing, one has to have all the papers in order, but you must know that from going to Vancouver.