I give up, the Clear Sky Chart is pretty darn accurate! The sky was pretty unfriendly tonight, but I went out anyway at 9:30pm, lugging my telescope around 1/2 mile to a nearby park. Fortunately, the city replaced the infields of one of the ballfields with astroturf, so the ground wasn't too wet to work on. I unpacked to a pretty cloud-covered Moon. Once things cooled down a bit, I set my sights on the lunar surface, checking out the Sea of Tranquility (Apollo 11 landing site), craters Plinius, Copernicus, and Kepler, and a few other things that I found interesting. The clouds frequently obstructed my view, but those times proved welcome as breaks because I didn't bring a chair.
Once the clouds started to break a little, I was able to make out Alhena in Gemini but not much else. As the clouds broke a bit more, Castor and Pollux became visible and I split Castor cleanly at 240x.
I then set out to see the M44 (Beehive Cluster) for my first time. It took me a few minutes of hunting before I found it. Forget about naked eye in NYC... 12x25 binoculars (which admittedly are not good for astronomy) didn't pick it up, and it was faint in my 9x50 finder scope. At 48x through the XT8, however, it really shined!
The story ends with the wind picking up a LOT and the cloud cover returning. Tomorrow is another day!
*Also, I was reading a star chart by a red LED flashlight when an unmarked police car pulled up to find out what I was doing. The officer who was driving seemed a bit disappointed that it wasn't "a bunch of kids hanging out" that they could kick out of the park. Once I explained what I was up to they went on their way and left me to my (cloudy) sky.