Ask GGW: Graduate programs?

Reader Leo writes,

I am an avid reader of Greater Greater Washington and have really learned so much since I’ve started following the blog. I would like to pursue a graduate degree in Transportation Planning. Since graduating I’ve worked for a completely unrelated organization, so I don’t really have any connections to anyone in the field. What programs are worth looking at?

People periodically email asking questions such as Leo’s. I do not have a degree in an urban planning-related field, but many of you do. What should people interested in a planning career consider? What are the pros and cons of various degrees? What programs are best, both in the region and elsewhere?