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1.
Surfing the urban dictionary on "random" due to a combination of intense boredom and will to expand your street knowledge.
"Dude, what have you been doing all day?"

"Nothing man, just a bit of urban surfing"
by Steve Gremo October 11, 2006
 
2.
not holding on to anything while riding the subway train, when the train turns, stops, goes etc. you get jerked around and have to "surf" to maintain balance

derived from the natural position your body takes in order to maintain an upright position

can be both purposeful or accidental (e.g. children are often urban surfing for fun, while adults are forced to urban surf when the trains packed)
The other day these two kids almost knocked me over because they were urban surfing from 110th to 96th. Nobody can survive those rickety turns when the train cuts through the park!

The ride to Coney Island was so long that we were urban surfing just to pass the time.
by bambugg10 July 24, 2009
 
3.
old school street skating in the city,
hey man lets carve up the streets this arvo, nah i cant go urban surfing today i got other stuff to do,
by Hallzee June 15, 2007
 
4.
Taking a board of some kind (eg. body board, surf board) just after it has rained heavily and using it to surf across the areas of parks, backyards, golf courses or any urbanized locations where there is enough water for the board to skim across with small amounts of kinetic energy, usually created by running up to and jumping on the board.
"The Baseball field is flooded! Let's go urban surfing!"
by MarkMash17 February 05, 2008