Some links and places to start for outdoor bouldering and rock climbing in New York City etc.

Central Park is good:

• The "Classic NYC Bouldering Guide" circa 2000, large .PDF download here.
• http://www.beta-boy.com/nycboulderingguide/index.html
• http://www.rockclimbing.com/routes/North_America/United_States/New_York/New_York_City/Central_Park/
• http://www.climbnyc.com/climb/
• Think Cat Rock, Chess Rock, Rat Rock, and Worthless Boulder (aka Rap / Needle Rock) to start.

Fort Tryon / The Cloisters, Van Cortlandt Park at the Northern end of Manhattan and into the Bronx

• http://upstatemanhattanboulderer.blogspot.com/
• http://scottsnelling.blogspot.com/search?q=1%2F9
• http://scottsnelling.blogspot.com/search?q=+Uptown+Boulder+Exploring
• http://www.dabtronics.blogspot.com/

Harriman State Park:

• You can take NJ Transit rail with your crash pad to the Tuxedo Station, walk left down the highway (opposite the direction the train came) and when you see a small house with many flower planters take a left and cross over the tracks behind the house, you'll see a trail into the woods that leads to a sketchy closed bridge, cross this long narrow metal bridge to a parking lot, follow right underneath the highway and turn left up the hill, continue about 1/4 mile up on the right past a couple of houses you'll see the white trailhead markers.
• The White Trail (goes up to the right, paralleling the house road), Blue Trail (goes up and left deeper towards the Appalachian Trail), both have big rocks for many miles that are fresh for climbing
• http://www.getbeta.com/rock_climbing_locations.asp?locID=5436

The Ice Pond, located near Brewster, NY

• Take the exit for route 312 off of interstate 84. Head east on route 312 and make a left onto ice pond road, which is just before the rail road tracks. Follow Ice Pond Road for about 1.5 miles and park at the obvious pull-off on the right hand side. Boulders can also be found down the road past this parking area off to the left, roadside.
• http://www.listphile.com/Open_Climbing_Atlas/Ice_Pond
• Problems: Evolution Boulder, Mercury in Retrograde, Catharsis (V10)

Bennet's Pond (Ridgefield) located near Danbury, CT:

• http://www.rockclimbing.com/routes/North_America/United_States/Connecticut/South_West/Fairfield_County_Area/
• There may be more parking other than the main lot, because if you look at the maps on the above link, it's a couple of miles walking to the 3 main boulders. Ape Boulder was pretty good, but a long walk.