The mid-Hudson valley is beautiful, and lots to do in the funky, old Hudson river towns and the quaint villages of (for instance) Dutchess county. There is art in Beacon, the Walkway over the Hudson in Poughkeepsie, the Roosevelt home and library, and Val-kill in Hyde Park--also the Vanderbilt Mansion...maybe the Mills mansion in Staatsburg (not sure if it's open), and Norrie Point state park. Lots of quaint boutiquey shops in Rhinebeck--a good bookstore and art supply shop (I know you aren't shoppers, but just saying)...and the Beekman Arms--America's oldest inn. There is lots of antiquing in Hyde Park and Rhinebeck. If you cross the Kingston-Rhinecliff Bridge, Kingston has the Rondout area with the Hudson River Maritime Museum. If you go up the Thruway to and cross the Rip Van Winkle bridge, there is Olana (you can see it as you cross the bridge), the home of a famous artist. (Frederic Church? I should have looked it up for you.) Hudson itself is artsy--lots of galleries down Warren St. Forgot about the Hudson river lighthouses--there is one off Saugerties and one off Hudson...others, but I'm not too familiar. Albany is an hour from Kingston--not quite as far from Hudson--there is the Empire State Plaza and the New York State History Museum is very good. Personally, if I were going to drive all the way over to Buffalo and Niagara Falls--agree that you want the Canadian side, so make sure you have your passports--for a child as young as yours I believe they will want the birth certificate--check this online--I believe they don't need their own passport for Canada until they're 15, unless you're flying in on a plane. Anyway, if you're driving up from NYC, I would frankly rather go up to Montreal--gas up first in Plattsburgh, and maybe just grab a sandwich and catch your breath--and then I'd recommend the old part of Montreal--great food, and we enjoyed the Archeological Museum, which is right there on the river in the old town. Be ready for French road signs and speed limits in kilometers. (Hint: "Travaux" means "roadwork". There is lots of "travaux" in the summer. ) If you do the Niagara Falls thing, I know that Niagara-on-the-Lake is supposed to be great. And getting out of sequence here, but I agree with the person who recommended Lake George--Fort William Henry was interesting and kid-friendly. I can't say about Fort Ticonderoga--it's on my list, but I've never been there. Old Fort Niagara and the park there is Youngstown, NY (i.e. Buffalo) is probably worth a look. I get their newsletter, but have not been there since I was a kid. Your problem on this trip will be narrowing things down--there is far more to see and do than you will have time for. If you take 90 from Albany to Buffalo, there is a lot of history in the Mohawk Valley, too--Johnson Hall, Fort Stanwix, Oriskany Battlefield. Way too much to fit in.