We lucked into a good picking orchard. Some places are too theme-park flavored. We wanted just a farmer with a back forty and a bunch of trees. We payed $15 per half bushel I think and the guy was really neat and real. You can read more about his farm at the Mister Apple website.
A strong bonus was the orchard's location in the middle of an upstate historic district. High Falls, NY (Ulster County, right next door to New Paltz) has a great actively maintained museum and a Fraunces Tavern type of Dutch-era Inn.
There were (in descending order of deliciousness) Winesap, Jonagolds, MacIntosh, Gold & Red Delicious, and Cortlands. In the picture you can see the applepicking poles we used. The Hudson Valley has a lot of picking spots. Check out the map at the very bottom of the Hudson Valley webpage.