While I was in Boston for a month recently on a research trip, my husband and I had some interesting exchanges via text and Twitter. He was often curious where in the city I was and how I was getting from place to place. On more than one occasion, after looking at Boston via Google Maps and other online tools, he told me the place was hopelessly confusing. When I returned home he referred to “five-dimensional Boston” and we joked about the city being like an M.C. Escher painting. That got me thinking about both the geographical and historical dimensions of this old city, and how together they’ve made Boston qualitatively different than any other major city in the U.S.

Boston is confusing, and while I was there I often had trouble getting around or knowing where I was. To be sure, part of this was just being in an unfamiliar place (I’m from Oregon), but it’s also true that Boston has a uniquely chaotic geography. Boston is shaped kind of like a badminton rocket, with the rounded knob being the tangled mass of the central city–the North End–and the body of the rocket being Back Bay, the South End, Roxbury, etc. The city got this strange shape as a result of its original settlement in the 17th century. In those days Boston was a cherry, a peninsula of land sticking out on a narrow spit from a C-shaped harbor surrounding it. Most of the modern city, especially the Back Bay area, is built on filled-in land.

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Boston’s historic district and its financial center are on top of each other–literally. Few of the streets here make any sense.

I moved about the city mostly by subway and on foot. The driving habits of Bostonians terrified me, and in any event it wasn’t practical to get a car for a stay of only a few weeks. Although I came to know the subway–the “T”–quite well, it still had the ability to confuse and surprise me. I was often surprised, for instance, how close stations are to each other on the surface, when down in the tunnels it seems like a much longer journey between them, or is impractical to go between them at all. For example, the Massachusetts Avenue T stop is literally two blocks from the Symphony stop. You could walk between them in less than five minutes. But as they’re on different lines, it would be a fairly arduous journey to go from one to the other on the subway, and involve various transfers and back-tracking. One time when I ran out of money on my subway fare card I decided to walk from the Massachusetts Historical Society to the North End. It was about a half-hour walk, but I must have passed 15 or 20 T stations on various lines.

I also often didn’t realize where I was in relation to other landmarks. My “home base” was the Massachusetts Historical Society, on Boylston Street, next to Berklee College of Music. Each day while there I’d see hordes of people in Red Sox gear streaming past the windows on foot, but I didn’t quite realize how close I was to Fenway Park stadium–only a few blocks–and that there was, in fact, a shortcut that led directly there from the library. The surrounding areas were hidden from view by a tangle of freeways, some overpasses, some under, and I couldn’t see the massive Citgo sign that’s very close to Fenway. (I assumed erroneously that because I couldn’t see the Citgo sign, I must have been far from the stadium). By contrast, the first time I tried to go to the North End–the old historic heart of the city where some Revolution-era sites are–I couldn’t find it. I knew it was somewhere near Fanueil Hall, but even walking with Google Maps on my phone as a guide I wound up lost in the financial district. The streets in this part of Boston really do loop around each other. What I thought of as the North End was very small: a cluster of old historic buildings, dropped like a child’s toys among the tall steel grass of skyscrapers.

Parts of the historic district also amazed me. Despite cobblestone streets, landmark signs, antique graveyards and 18th century buildings, much of this area is still a real living neighborhood where ordinary people live. Nowadays we’re accustomed to seeing historic districts as roped-off museum showpieces, or at least infiltrated by the foot soldiers of gentrification, like swank restaurants, real estate offices and “hipster” bars. Not so. Literally a block from Paul Revere’s house I passed a blue-collar family moving out of their apartment, a man and a woman chattering in Spanish while trying to strap a mattress to the roof of a car.

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This historic neighborhood, where Paul Revere lived 250 years ago, is still every bit a vibrant and living place today. “Ordinary” people still live there, as they have for centuries.

How did Boston get so confusing? Its history has a lot to do with it. Boston is one of the few large cities in America that was initially created before any sort of urban planning existed. It grew organically at first, thus replicating the clustered, tangled and accidental look of European cities like London and Paris. Even New York did not develop this way; the 1811 “gridiron” plan for Manhattan ultimately co-opted the tip of the island which was much more chaotic. By the 19th century, when most American cities grew in earnest, there were, if not semi-governmental planning authorities, at least informal collusions of builders and pavers who made sure cities grew in easier shapes.

But Boston’s history is by no means homogenous. Mixed in with the 18th century buildings and cobblestone streets are arrow-straight “luxury row” neighborhoods, built mostly in the late 19th century to cater to rich people (Commonwealth Avenue is one such area), and more traditional 19th and early 20th century clusters of working class housing. Add to this an even more modern layer of office towers and modern infrastructure, and Boston becomes not so much a dimensional vortex, but a layer cake, mixing various eras and concepts of planning, construction, commerce and history. Again, few cities in America are quite like this.

When I got back I was fond of telling people that my trip to Boston was both awesome and infuriating, and these attributes existed in roughly equal measure. To steal a famous line from Jimmy Breslin regarding New York, it’s easy to love and hate Boston equally. Surely it is one of the most American of all cities, and will continue to be a confusing place for as long as it exists.

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