I sit in restaraunts at lunch all the time with a chess book and a board out, playing through some games or whatever, and people always look at me funny, or come up and say "Hey, are you playing yourself? Are you winning?"
Annoying cretins. Go away and let me study! 
my wife and i played a couple of years ago in the last row of a cinema watching the movie--knocked up. there was a lady, probably in her 50s, sitting one seat from mine. risky, but totally worth it. totally. i won with mate after 18 moves or so. it had to be a quicky since the theater was nearly full.
fun times
lmfao at the first post, ive played in the parking lot under a building with a security guard, and ive also played at a construction site
Ahhh that brings back memories... my girlfriend and I played chess up on a Soho rooftop in the summer of 1982... a low rooftop, so I'm sure all the higher buildings had a clear view of our game. And what a game it was -- long and very positional. Such a great game and I can't remember who won.
As a crew chief, I played chess with my magnetic set and board with the rest of the crew members on board a KC-135Q while refueling an SR-71 Blackbird or B52 bomber at 32,000 feet over Southeast Asia in the early 1970s. I always had a pocket chess set on the flightline or when flying. I once played blitz chess for 20 hours straight at a USO club in U Tapao, Thailand. That was my crew "rest."
Many years ago, when I studied at the university, a few times I played during the lectures with the guy who had a 1st category - probably something about 1900 USCF. We used a small chess set, he played not looking at the board and tried to write the lecture, I played normally and didn't even try to write down anything. I don't remember what was the result.
Online. It doesn't gt any stranger than a virtual free for all with no door man and hard to enforce rules.
At many Amsterdam coffee shops. Not really strange but certainly enjoyable
On top of a Tikal (Mayan) pyramid in Guatemala with a friend.
It's in the middle of the jungle, with plenty of squawking parrots and the occasional monkey jumping between the trees. Such a rich place...full of tourists these days :(
ooh in the dressing room inside of the mall on a not so busy day it was ammmaaazzziiinggg oooh are we suposed to be talking about chess idc best 15$ ever spent
I'm very "old school" so i usually just play/analyze at home or at tournaments, and since joining chess.com online..... doing "forbidden" things in the shadows with a chess set would be pushing my "envelope"....good question however....
At a university, a friend and I both worked in the cafeteria in the dishroom, to make some cash. The floor was an alternating square pattern. He worked on the other side of the room and had to come to my side throughout the shift to bring carts of clean dishes. We started playing chess in our heads, using the floor to help out remembering the position. So he would come in and announce his move and then on the next trip I would tell him my move. People would walk by and see us both staring intently at the floor. Probably wondering about our sanity or our soberness. It was a fun way to pass the time in an otherwise dreary dishroom.
maybe not the strangest places but ive had a few interesting experiences playing chess
i drank a pint of burbon on night and ended up in my friends kitchen, sick drunk in his sink, he had a chess board on the floor and he would call out the move and id respond verbally...he thought he could beat me if i was blind drunk, he was wrong...
i played "blind fold chess" with a schizophrenic in a mall. we didnt have a board so we just told each other the moves and played in our heads.
in a mental institution on the phorensic (criminaly insane) unit, well, every where in the hospital was odd really...
in bathrooms with the travel set. out in the middle of nowhere camping
I played against my brother in the gallery of an amphitheater ruin in Caeserea, Israel in December 1998. That was definitely the strangest place for me.
We were tired of touring and stayed back to play while the tour continued.
In a college game room. The jukebox was playing, people were talking and video games were making noise. In a strange way the noise may have helped our concentration.
I played in front of a mall with this older man and lost; I went home embarassed because there always has to be 1000 people watching. I reviewed some good openings, came back the next day, and crushed him with the Queens Gambit. :)
i got kick out of a bar once when i was 15. it was a place where many of my small towns older folk hang out, drink beer and shoot pool. i went in to play chess and everything was all fine and dandy until we started playing for money and i kept winning. the barkeep decided that an under age chess hustler wouldnt be good for business and had the "bouncer" (a 65 year old man) escort me to the door.
2000 feet up the face of El Cap.
I played a game with Steve Schneider and beat him on a board we made with triscuits and wheat-thins.
Raisins for pawns, assorted nuts filled in the minor and heavy pieces, dried apricots for Queens and figs for Kings.
Raisin to Wheat thin 4 is strong, but my defense of Cashew to Triscuit 6 put his raisin under immediate pressure.
Love this story, Also billwall's was good. When is your book coming out?
We all know that chess in public can be quite risqué, which for me only serves to enhance the excitement of the occasion. Thusly, my answer is going to fall under that category.
A few years ago I was at a bar with my friends when I ran into a girl I went to high school with. Well, one thing led to another, and with the MD 20/20 fortified wine (strawberry kiwi) doing the talking things escalated to the point where we had to play some chess and we had to play it NOW. We went to my car and drove to a slightly secluded but still visible area behind a parking lot where we just went at it on the chessboard. I still remember her taking my queen with her knight and me being so upset that I just kicked her out. Haven't seen her since.
Those were the days.