I can't get it crash on a path that short. I can produce an error message if I push it beyond the 254 limit, but you can work around that by applying the filesystem namespace prefix:

<code>
import os

path = "c:\\" + "\\".join (130 * ['xx'])
os.makedirs (path)
#
# will fail more or less violently
#
path = "\\\\?\\" + path
os.makedirs (path)
os.listdir (path)

</code>

Probably related issues:

http://bugs.python.org/issue9246
http://bugs.python.org/issue4071