This is a game that I invented a couple of years ago. It's not actually been played yet as I'm waiting for it's namesake Henry Holland to visit and come and play.
OBJECT OF THE GAME.
Manhattan has a lot of avenues (at least 12) running from north to south. Using aesthetic passion, design judgment and alcoholic verve the winner will be the person who manages to find the most interesting/visually appealing spot on those avenues.
HOW TO PLAY.
Choose a staring point. I've no wish to be too prescriptive but I would suggest that you begin on either the east or the west side, and avoid Central park as from my last look it doesn't have any avenues running through it.
Then find a bar, have a drink. Continue this process as you cross the island of Manhattan. When crossing an avenue glance north and south as is safe to do so (please don't get run over or otherwise die). Examine briefly the scene that greets you there. Look for anything, architecture, the way the clouds are moving, the street life,anything and then find the nearest bar on the other side of the avenue, drink and discuss. You may want to take notes, digital pictures, whatever. As I said above, do not spend ages dawdling in the middle of the road, you will die. You could do the viewing from the sidewalk, perhaps setting your group a time limit. The key is that you get across Manhattan and you have a drink between each and every avenue. Maintain a straight course, for example, if you choose to walk 34th street, then try as hard as possible to stick to 34th street, deviate only in the search for suitable drinking establishments and be sure to return swiftly to your chosen course.
I think the winner is the most passionately drunk person who can still hold a conversation together, well, everyones a winner! As mentioned above, avoid Central Park. Trees are cool but you can't get a beer in them.
I'm waiting for Henry Holland to play but if anyone tries this in the meantime, please let me know how you get on.