Suggestions for Weekend Trip from NYC ?

Cold Spring and Cold Spring Harbor are two very different places . I believe you mean Cold Spring (the one on the Hudson). Great hiking nearby if you do .

 

Peekskill. Awesome, scenic train ride up, 5 minute walk to brewery. Good food and atmosphere , been awhile since I their beer though. Used to do this trip a lot until NYC beer scene exploded.

 

Northport on Long Island.

Little town with good food and you can visit Sand City.

 

Forgot about that one, yep, would be a great trip too.

 

Just throwing this out there even though it's a small diversion from your criteria. My GF and I recently spent a long weekend in Vermont. 45 minute flight from JFK to Burlington. It was only $50 one-way per ticket (we drove back). The airport is just a few miles from downtown. Great food options and, with the addition of Foam Brewers, you don't have to venture far off Church St at all. Despite being a college town, Burly was pretty quiet while we were there. The Fall Foliage crowds are pretty much long gone by now.

 

Northport would be a good one, but the town is pretty small and there's not too much to do without a car (in my opinion). But Sand City is super great.

Cold Spring is a really nice town, but Beacon probably has more to do, especially if you're going for the whole weekend. Draught Industries has a very nice tap list (https://www.beermenus.com/places/17907-draught-industries). There's a number of good restaurants, cool shops, art museum, etc. Mount Beacon is a really cool hike, there's an abandoned train station at the top that used to be part of an incline railway. You could always take a quick cab to Cold Spring or hop back on the train if you wanted to check that town out as well for an afternoon. It's only about a 10 minute drive or so.