I wrote the below about six years ago (just a few small edits & smileys added), let me know if you have an additions for me!
One of the reasons people like big cities and New York in particular is that : whatever you're into, chances are you'll be able to find some other people who are into it also. Over the years (only three so far) I've found a number of good places to meet up with other reasonably strong chessplayers and get some good games in. Its a nice thing, to be able to have an instant connection and mutual respect with someone who may not even speak the same language as you. Being able to play on the internet is a great thing but theres something about sitting eye to eye with the man (or woman) you're playing and physically moving the pieces and hitting the clock, spectators gathering round to observe. Its fun. So without further ado, here are my "reviews".
Places to play in Manhattan :
This is one of Manhattan's more famous parks (right up there with Central). Most of the chessplayers hang out in the South-West corner of the park and most of them do play for money. However if you bring your own set and there is a free table chances are pretty high you'll be able to find a few people who are willing to play a friendly game with you. Washington Square Park
The New York Public Library is on the 5th Ave side. In the summer months this is a very popular chess spot. Usually a good mix of blitz & slow chess. Bring your own set or wait in line to try to get into a game (the loser will get up & the next in line will play the winner, usually groups max out at 4 or 5). The park is located bewtween 5th and 6th Ave. and 42nd St, three blocks west of Grand Central and one block east of Time's Square. The players hang on the 42nd St. side, not the 6th Ave. side. For tourists, the famous Bryant Park
The "glass house" is a large glass building located in Manhattan between 52nd and 53rd street (you can enter on either side) and between Park Ave. and Madison Ave. For awhile I think the building's owners were not letting people congregate there (due to the semi-recent terrorist attacks) but now everyone is back and ready for action! You get mostly speed players here, genrally around or above my strength (my blitz rating is about 1450, "The Glass House" in 2002, now it's higher!). Its a really nice place to hang out, especially in the wintertime when its far to cold to spend any time in the parks. Alot of older guys, no one really gambles, everyone is usually pretty friendly and will let you get in on a game or two (provided you're willing to wait). Its also a very nice place visually, the ceilings are very high and there is a waterfall on the wall and planted trees (real trees of course!) and even a bird or two. During the day they sometimes have a man who plays piano in the center of the foyer. This is one of my favorite spots in Manhattan, I always run into someone I know. Oh, by the way, its closed on weekends (on weekends many players head to the nearby Sony Building at 55th between Madision and 5th Ave.)
Places to play in Queens :
This is an excellent place to get a friendly (non-gambling) game. There aren't alot of tables (five I think) but if you're willing to wait chances are you can get a game. The park is located off Queens Boulavard near the F train (71st Ave). MacDonald Park in Forest Hills, Queens Note, I haven't been here since 2002 but I imagine people still play here.
This is a classy establishment. I often play pool there or air hockey with my girlfriend. Many evenings you'll see people playing chess and backgammon as they eat and drink and watch the big screen TV (usually a Greek channel). The best thing is, the house will give you a free chess board and set to use for free (they just need an ID as insurance). One note, if you spend time there you are usually expected to buy something, I usually just get an apple juice if I'm not hungry. Steinway Billards in Astoria Note, I haven't been here since 2002 either but I imagine players still hang out & if not, it's still a nice place to catch a game of pool.
I'm sure there are many other spots around town to play chess. There's one Starbucks on 125th St. where I've played a few games, there's also a spot off the beach at Coney Island where people play, I've only been there once and it was with my girlfriend (so I couldn't hang out long ). I'm sure there are countless other spots of which I am not aware. If you play in New York and know any good locations I haven't mentioned, let me know, I like exploring, going to new neighborhoods, testing myself against differnet players and experiencing the varied personalities that are attracted to this deep yet elemental game.
Note : If you go to some of these outdoor parks in the dead of winter you may be dissapointed but if its above 50 degrees (F) you'll probably find some players.
Video from Washington Square Park : that's my homeboy Raheem in the first half of the video (on the left)