Residents of northern New York State - the true Upstate region - know that the state consists of several regions. Namely, upstate, downstate, western (Buffalo and Rochester), central (Syracuse and Utica), and the city. (I like to think of Long Island as an orbiting moon, but it is better classified as a different planet all together.)
Albany is barely on the edge of Upstate, Poughkeepsie is NOT Upstate, and Newburgh is definitely NOT Upstate. It may be hard to fathom, but not everything in the state of New York revolves around the city, so therefore, everything above the city/Westchester is not Upstate.
Admittedly, Upstate may be "different" than New York City and other regions, but it is a term of pride, not a term of derision. Many ignorant downstaters (who probably don't recycle and drive Hummers) may not realize that Upstate is home to the Adirondack Mountains and the most beautiful natural areas of New York state. Always remember, not only does New York State have the largest, most culturally diverse, most amazing city on the east coast, it also has the largest tracts of pristine, protected wilderness lands east of the Mississippi in the northern, Upstate regions.
New York State is amazing, from top to bottom!
"No thanks, I am going Upstate to my cabin on Lake George."
"Oh wow, you are so lucky! It is gorgeous up there."
In rural New York State people will either use the NYC area or the Albany area as the marker for upstate. Some people from Orange County for example, say they live upstate and some vehemently oppose that designation, as Orange County is well south of Albany.
The word "upstate" has a particularly negative connotation and should be avoided. Few people like to be considered to be from "upstate", as it implies the antithesis of all that New York is about. "Upstate" is the N-word of geography and should be avoided at all costs.
Note: There is also a rare usage of "upstate" referring to everything outside of New York City, including Long Island and Westchester, just meaning New York State.
In the Bronx, anything north of Yonkers is upstate.
In Yonkers, anything north of White Plain is upstate.
In White Plains, anything north of Peekskill is upstate.
In Peekskill, anything north of Poughkeepsie is upstate.
In Poughkeepsie, anything north of Albany is upstate.
Westchester, Rockland, Orange, Putnam, and Southern Dutchess Counties.
Includes: City of Rye, Peekskill, Newburgh, Middletown, Beacon, Port Jervis, Yonkers, Mount Vernon, White Plains, ect.
So anything north of Poughkeepsie basically, like Ulster and Columbia counties.