James Oglethorpe arrived in 1733 with a plan. He laid out Savannah as a grid of wards, each one a city block organized around a central public square — open green space, planted, intended for the militia to muster and the residents to walk. Twenty-four squares were eventually built. Twenty-two survive. They are the city’s defining feature and also, accidentally, the most coherent urban shade system in the American South.
Each square is a square city block of live oak canopy, almost without exception. The trees in Chippewa, Madison, and Monterey are pre-Civil War. The Spanish moss they carry adds another layer of shade and a measurable drop in radiant temperature. Because the squares are arrayed in a regular grid — three north-south by six east-west, with the cross streets running through them — you can walk almost the entire length of the historic district by stepping from square to square, in continuous canopy, with only a sixty-foot exposure between each block.
The picks below are a single connected route plus a few useful detours. Start at Forsyth Park at the southern end and walk north toward the river, square by square. The shade is densest in the middle squares; the southern ones (Forsyth, Whitefield) have more open lawn. We avoid Reynolds and Johnson squares at midday — the loss of their canopy in the 1960s left them brighter than the rest. A practical note: the squares are crossed by cars on the cardinal streets; the route assumes you’ll use the inside paths, which loop slightly longer but stay in shade.