Chicago to New York

If we were to drive, we would go around Lake Michigan towards Grand Rapids then cross East to Sarnia where we would stop over for the night. That's 5h30 drive so a full day driving with breaks. Niagara falls are 3h drive away which could be done the next day.

If you drive just do the drive in a day. It'll be long, but it'll save you time for exploring later on. An eight-hour drive still allows for some short stops along the way.

We could stop at Rochester or Syracuse then hire a car for 2 days and explore the lakes (go to Watkins Glen), then take the train again for the second leg to New York. Has anyone done anything of the sort? Does it seem doable?

This is silly. Spend a lot of money for a train, take time to rent a car, explore, take time to return car, spend more money for another train. Rochester is only 1.5 hours by car from Niagara, Syracuse is 2.5, and both are detours from the Finger Lakes.

Just rent the car in Niagara or Buffalo, and drop it off in NYC. If you drove from Chicago, just keep that same car through to NYC. This would definitely save you time--you can be in the heart of the Finger Lakes region in just two hours, rather than dealing with being out of the way and dealing with rental agencies. It may also save you money. Five tickets for the train, twice (thrice if training from Chicago), is not something to overlook.
Also, on your way into NYC, you can stop in the Catskills.

The train Between Chicago and NYC is never on time nor a very good train route for anything.

Its a good 12 hour drive, times with traffic getting out of Chicago and coming into NJ/NYC...timing is everything. Basically, dont be in either city rush hour, which is 7am-10am and 3pm to 7pm...

I have made this drive many times, usually via motorbike, and make a fishing/hiking trip out of it, by staying north of I-80 once on Pennsylvania...

I usually beeline it 6am from Chicago to Ohio/Pennsylvania border, then head north on I-79 to Oil City, and either camp my way along the valleys and rivers and parks and state forest, or get hotels/bed and breakfast.

This is gorgeous countryside, lots of nature, and some pretty nice hiking trails and parks too...but you have zig zag.

Places I like to camp-

Minster Creek in Allagheney NP
https://www.fs.usda.gov/recarea/allegheny/recreation/camping-cabins/recarea/?recid=6104&actid=29

This park is the darkest area for star gazing the night skies on the eastern seaboard.

https://en.wikipedia.org/wiki/Cherry_Springs_State_Park

This park and campground has a swimming pool, and miles of hiking trails in the hemlock forest.

https://www.dcnr.pa.gov/StateParks/FindAPark/HynerRunStatePark/Pages/default.aspx

You can fish and swim in the river in the park, great area for hiking and biking.

https://www.dcnr.pa.gov/StateParks/FindAPark/LittlePineStatePark/Pages/default.aspx

The state parks in this entire region are very nice in Pennsylvania, a family atmosphere everywhere...blows away anything Niagara Falls has to offer, which to me is a tourist ghetto and not worth the time at all...

I would stop or head to downtown Cleveland for Rock and Roll Hall of fame & Baseball, or downtown Pittsburgh, or Philadelphia, long before going to Niagara falls...I cant imagine what the crowds and hell is there in July...ugghhh

And I love waterfalls, been to the biggest in Central America, SE Asia, China, and EU...

Thank you for your input about the leg from niagara falls to new york. You are right, renting a car makes more sense. I spent so much time thinking about different options that the practicalities escaped me.

That's fantastic info. Thank you. I will look at those links as soon as I have a bit of time.

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