I am also an ex-Noo Yawker (now in the mountains of NJ) but I have been all over the place on weekend trips.
Here are my suggestions. BTW, when are you planning on going (Winter, Spring, Summer). Timing can make an OK trip into an amazing thing to remember.
Winter Spots:
> Lake Placid: Home of past Winter Olympics and beautifully situated in the mountains of the Empire State. Beautiful town with very nice views. Can visit all the Olympic event places and watch future gold medalists working out.
> Bed/Breakfast or Cabin in Vermont-NH- Maine for a romantic getaway. Helps if you have 4-wheel drive. Get a place with a fireplace and a bear skin rug.
Spring:
> Washington DC - if only just to see the cherry blossoms.
> Poconos - used to go their all the time with my friends (family has a house about an hour in from the Delaware Water Gap). Go rafting down the Delaware or Lehigh River before the spring melt dries up.
> Niagra Falls
Summer Spots:
> Montreal! Great in the summer with their huge jazz festival and their Just For Laughs comedy festival. And you don't have to speak French to enjoy the place.
> Rehobeth Beach, DE - great beach town filled with things to do. Fantastic shopping at their outlets, too.
> Duck, NC - a great beach place... but pricey. Kitty Hawk is also nearby.
Fall Spots:
> The vinyards of Long Island (north of Montauk. A great day trip with wine tasting galore as you travel down the highway. Fun and romantic day or weekend trip.
> Fall Foliage Fantasy around the Hudson River Valley - West Point is there and perhaps some of the most incredible views of nature in NY state.
More to come after I eat breakfast.
- Ed