The fastest way to understand a city is to run in it at 7am, before it has decided what kind of day it is having. You see where people actually live, which streets wake up first, and how the place fits together in a way no map gives you. These five reward the effort.
Montreal
Up through the Plateau and onto Mount Royal, where the gravel switchbacks give you the whole island at the top. Humid in July, brutal and beautiful in February, and the only major city where a January long run is a legitimate conversation topic. Go up the stairs if you want the climb, or the carriage road if you want to keep running.
Tokyo
The Imperial Palace loop is five kilometres of almost perfect running surface, and at dawn it is full of people who treat it as a daily appointment. Run it twice, then get lost in the side streets on purpose. The traffic lights are the only thing that will slow you down, and even those feel orderly.
Paris
Along the Seine below street level, where the traffic noise disappears and the bridges arrive at a satisfying rhythm. Early enough and you will have the quais to yourself apart from the rowers. Cross at any point and run back the other side; the view changes more than the distance does.
Boston
Out along the Charles, over a bridge, back on the other side. Flat, scenic, endlessly extendable, and thick with runners who are all quietly assessing your form. The loops come in convenient sizes, so you can decide how far you are going while you are already going.
Chicago
The lakefront path, north or south, with the water on one side and the skyline on the other. Exposed to the wind in a way that will teach you something about pacing — run into it first, so the way home is the easy half.
What travels well
One cap, one pair of shorts you trust, a layer that packs small. You will wear less than you packed, and you will be glad you brought the cap.
Our city series caps are in Marathon Cities.