What's the farthest upstate I could live and realistically commit to the city three days a week? I was thinking Woodstock or Saugerties, but according to Google maps that's a two-hour drive each way or three hours by public transit each way. Was hoping for one hour by train from Grand Central or Penn. Looking to be in nature, near a cool town upstate, but not so far that commuting to work would be too hard. I do have a car but prefer not to drive into the city all three days.

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One hour from Grand Central only gets you to northern Westchester. Speaking as someone who grew up there.
The hour away places aren't really putting you in nature. The cooler places, as far as up-and-coming towns are in the 30-45 minute range. If you follow the Hudson line you can at least get some nice views.

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Tarrytown, Ossining, Croton on Hudson. Anything north of Peekskill will be more than an hour to and from Grand Central.

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How about Connecticut?

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Look in the Harriman area and below. The port jervis line on NJT is your friend west of the Hudson.

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That can be a little tricky, getting out beyond suburbia but within two hours isn't so easy. I knew someone who lived in the Lehigh Valley in Pennsylvania and would come into Manhattan some days, and that was two hours by car. Maybe think about someplace in central Jersey? I guess it depends what exactly you're looking for, if you want rural and not suburbia you might have to extend that range.

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Looking for towns like Woodstock, Beacon, Hudson, Saugerties? Little centers with some life, opportunities for socializing with ex-NYers, but want to find a cottage with a yard for a garden. Would love to go on wooded hikes with a view at the end. Commute 1.25 hr/way (train ride) at the most. Not looking to become a rural recluse or suburbanite. Would love to still be connected to the city three days a week.

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The only way I can pull it off is that my wife does not work in advertising so don’t feel so bad. Look at north eastern NJ or honestly rock away. If you want recs for your trip feel free to dm

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I just drove back to Queens from my place in Saugerties today. 3x a wk is way way too much, with traffic sometimes it’s over 3 hours. It’s a great area though.

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90 minute metro north train ride gets you to Southeast which is in the upper Westchester NY/ CT area. More affordable than lower westchester and more scenic. Dependent on the office location/ where you live but it’s a commute that’s around two hours Have known people who do that commute for years but it’s a commitment. I work remote primarily rn but do the commute when in office

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