“Riddle me this!” What do J.R.R. Tolkien and Bill Finger have in common? Why, they’re both riddlers, of course. The riddles found in The Hobbit are the focus a series of activities that direct learners’ attention to word relationships and word meanings. Class members go on a 20-minute walk and use an MP3 player to listen to a presentation about the riddles in Tolkien’s The Hobbit. Upon returning to the room, the class discusses the images and meanings included in this type of wordplay. Links to the podcast, discussion questions, and a comprehension quiz are included in the resource.