Around the corner? ;-)

hhp

http://www.societyofscribes.org/ in New York City.

If they don't have classes on Hebrew script they will know who will.

Another route: google "ketubah new york city" or "ketubot new york city

I think the Ketubah (decorative marriage contract) is an important part of business for a lot of Hebrew calligraphers. So you can ask these people.

Another way: google "scribe sofer new york city" that will get you the Torah scribes.

The book Michael mentions can be viewed on flickr:
http://www.flickr.com/photos/yaronimus/sets/72157594406774337/

I have an aunt in Jerusalem who maintains that Toby's book is the only one worth reading. I've actually found and ordered a used copy (even though it's online, it's awfully nice to have physical books). As to style—the traditionalist in me is tempted by Stam, but my main goal is to have a good foundation in lettering and alphabet "anatomy" to aid in designing contemporary Hebrew type, so something closer to modern Hebrew scripts might be better.

Despite growing up in Israel, I didn't get into typography until grad school in New York. My understanding of the Hebrew alphabet is scarcely better than a layman's, having read some essays (Raphael Frank's and others) and done some analysis of my own on readability and letterforms. Learning lettering in school was a great preparation for working with Latin type, and I'm sure it will be as effective for Hebrew. And as much as books are nice, I learn best from direct experience with another person.

Thank you all for the advice, in any case! I probably need to do some more research into the styles of Hebrew calligraphy before I seek out a teacher.