Plovdiv has many great stories and little cute anecdotes to pique your curiosity. These span over SIX THOUSAND continually inhabited YEARS! So, just like with Bulgarian Menus, you can choose a page (of history), something you like, and not really know what you're going to get at all. But what is sure is that you are getting a massive serving.
A more recent and very much unknown fact about this place, is that the third episode of Ukulele Road Trips Podcast was recorded there. It's an Easter special with plovidivy themed chit-chat, just what the place and season demanded. You should give it a listen I reckon.
If you like hills, cobblestones, nice views and Roman Theaters, you're in for a treat. They have respectively 6, a lot, a few, and one nice one. On the other hand, if you're more into 'walking only' high streets, well... you're also at the right place. Plovidv (and this is totally unchecked information by the way) has the longest in Europe! So you can take a stroll with your girlfriend/lover/trophy wife, or an ice cream, whatever makes you happiest, while under your feet silently snooze thousands of years of history. I mention this because they did recently dig up part of a Roman chariot racing track, but did not excavate the whole thing because that would have meant tearing the whole historical city center apart. Sensible thinking that.
In all these pages of the history-menu turned by a promenade in Plovdiv (and a great free walking tour), the humble story of a charming mustachioed man during the Communist Dictatorship caught my attention. Violinist Sasha the Sweetheart. Not the best name, but I'm guessing it sounds better in Bulgarian. A passionate musician, and as you can guess from his twinkling smile, a sweet humourous entertainer. Sadly, one joke too many, and to the wrong people, lead him to "disappear" all of a sudden in 1961, quite probably to a labour camp. Today, his beaming statue watches over the streams of sunglasses and tourists that pass by the old music school to take a peak at the Roman Theater.