Sep 25, 2026
Five to seven miles on a full day, on brick and cobblestone. Here is the map in your head before you arrive.
Train, ferry, or bus, then walk. In October, a car is the thing most likely to ruin your day.
The car, the big backpack, the new shoes, and a few other things you will regret by noon.
Any day in October, in most places, with some limits on masks and props. Here is how it works.
Cool days, cold nights, and wind off the harbor. Here is what each week of October actually feels like.
Warm layers, gloves, a charged phone, and cash. The rest is optional. The gloves are not.
Brick, cobblestone, hills, and 15,000 steps. Your shoes are the most important thing you pack.
Build it over layers, keep the mask off on the street, and make sure you can walk a mile in it.
Layers, a rain shell, and shoes you can walk five miles in. That is most of it.
Sep 24, 2026
Marketplaces open, glass pumpkins take the Common, and the Grand Parade closes the week.