When trying to convert a JPA object that has a bi-directional association into JSON, I keep getting
org.codehaus.jackson.map.JsonMappingException: Infinite
Also, Jackson 1.6 has support for handling bi-directional references... which seems like what you are looking for (this blog entry also mentions the feature)
And as of July 2011, there is also "jackson-module-hibernate" which might help in some aspects of dealing with Hibernate objects, although not necessarily this particular one (which does require annotations).