Cold Spring is a cute little town on the Hudson. No need to rent a car, you can take a day trip on Metro-North Railroad, which leaves from Grand Central Terminal.
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www.coldspring.com]
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www.mta.info]
The Berkshires, which includes portions of western Massachusetts and eastern New York, are known for fall scenery. It's about a three-hour drive from New York. You might consider an overnight stay in one of their beautiful inns.
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www.berkshires.org]
Long Island's wine country is beautiful in the fall, too. There's lots of info on the LI Wines web site, including info on bus tours of the wineries. There are lots of farms in the area with corn mazes and Halloween events.
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www.liwines.com]