Recommendation for daytrips out of GCT?

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On the Hudson Line (best scenery by far), Tarrytown is nice and close, but a bit of an uphill walk. Cold Spring is about 75 minutes from GCT and is a wonderful place to walk around (antiques, etc.).
 
Irvington (the station before Tarrytown) has a few nice restaurants right near the station: Chutney Masala, MP Taverna, and Red Hat.
 
right to Poughkeepsie take elevator up to Poughkeepsie bridge , walkway over Hudson back towards Cold Spring shop and have lunch.

nice place to railfan is at old Cold spring NYC station now great Hamburger and other things restaurant with view of tracks.
 
Cold Spring is the best choice. Spectacular views of the Hudson. Many restaurants within walking distance, but it is not 75 mi from GCT, more like 45.

Also the next stop is Beacon, which has the amazing DIA museum and a short walk up the hill to a great strip of restaurants. All a little bit more spread out than Cold Spring. Be sure to sit on the left side heading north.

Also, if you are the robust type and it's a spectacular day, check and see if your train (Metro North) will make the stop at Breakneck Ridge. This is a whistle stop for hikers, just a few miles north of Cold Spring with trails up onto Breakneck Ridge which work their way back to Cold Spring. The climb up the ridge can be done in sneakers, but it is not for the faint of heart.
 
Cold Spring has been my favorite for years. Great view of Storm King Mountain. View of West Point far down river across from Garrison. Great places for photographing trains both on the MNRR and CSX across the river. Remember to mount your longest range zoom lens on your camera. I have spent many a delightful hour in Cold Spring and recommend it.
 
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If it is more trainriding variety than scenery you're interested in....I would take a MN New Haven line train to Bridgeport, then take the carferry across Long Island Sound to Port Jefferson, than a taxi ride to the Port Jefferson LIRR station, then an LIRR train back to New York (Penn Station)....this would be best in the warmer weather, of course....
 
If it is more trainriding variety than scenery you're interested in....I would take a MN New Haven line train to Bridgeport, then take the carferry across Long Island Sound to Port Jefferson, than a taxi ride to the Port Jefferson LIRR station, then an LIRR train back to New York (Penn Station)....this would be best in the warmer weather, of course....
If you do this in the reverse order, i.e. NY Penn - Port Jeff - Bridgeport - NY GCT, you can take a pleasant downhill walk from Port Jeff Station to Port Jeff Harbor passing through the quaint village of Port Jefferson. You can catch a lunch or a snack at the numerous eateries that you pass on the way too. That is my preferred direction. The walk in the opposite direction is all uphill.
As a matter of full disclosure Port Jeff was my old stomping grounds since I went to graduate school in SUNY at Stony Brook, or in Stony Brook University as it is referred to now.
 
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