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How far up the Hudson....

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Hi, I'd like to do a day trip in May from Manhattan going by train up the Hudson (Metro-North) to a nice town then renting a car to do a driving loop before heading back to Manhattan by train again.

I'll be starting early in the morning then returning the car around 6.00pm, so a full day.

I'd like to see maybe Kykuit or the Vanderbilt Mansion, or both, though I'm not sure if it's possible to see both in one day. Plus quaint towns and villages and nice driving scenery.

I'm thinking Enterprise for the rental car, they seem to have lots of locations and will pick you up to collect the car.

I will be solo (from Australia) so I would prefer picking up a car in a quietish place.

So my questions are:

1. Which of these historic places would be the most impressive to see?
2. How far up the Hudson should I go for a scenic train ride before getting off to pick up a car? I was thinking Tarrytown (for Kykuit) and Poughkeepsie (for the Vanderbilt mansion).
3. Any suggestions for a nice driving loop for each of these places before going back to return the car and take the train back?
4. Is Enterprise a good company for a rental car?

Thanks for any suggestions or advice.

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