Now of course I went to college there and got my first post-college job there, so there are a lot of reasons Boston is nostalgic for me. But I have spent about 5 years in several cities and the Boston metro seems the most dense in this regard: more so even than Seattle, where I actually grew up. Of course college is a formative time, but then again it's been quite a while since I was there, so age has also dimmed some memories. All in all, though there are confounding factors at play, I still think the urban design is significant to how I remember it.
1. Walkability strengthens memory
Or perhaps that should just be that walking does. I have memories of random things that happened on random street corners or pedestrian spaces, and it seems to me that their very frequency comes from the fact that I was free to walk a lot. When you drive everywhere, you drive directly to the destination, especially if you have Iowa Rules to play with. This means that whatever happens outside a car (and for me at least core memories tend not to be from inside the car, but from where you get to outside of it) tends to happen at the same spots, overlaying each other. Individual spaces may then become extra special, but the overall urban terrain is spotty, rather than continuous, in memory.
Take this spot:
If I was in a car this literally wouldn't happen -- or if it did it would happen directly in front of my classroom, rather than creating a separate space with separate memories attached.
Because I walked everywhere, because I could and the urban design encouraged it, Harvard Square and its associated areas are full of these little individual places of memory.
2. Transit-Orienter (Memory) Development
I propose that transit also plays a part in this kind of memory development. Yes, it divvies up the city into little chunks around transit stops/stations (Harvard/Porter/Davis, Copley/Prudential/Symphony), which is superficially like what I described with cars above. But! It produces walksheds around the transit stops, rather than direct door-to-door connections. To go to the Davis Square T station is not the same as going directly to the JP Licks near that station, even though it is very close indeed. And the further your walk, the more you get the above effects triggered by the station's walkshed.
3. The grid impedes
Now obviously grid systems have advantages. John Mulaney has a good bit on that. But Boston as a metro area has notoriously non-gridded streets and I suggest it aids in the creation of distinctive memories in two ways.
First, the inefficiency: annoying as lacking easy wayfinding is, it creates space for entertaining and memorable interactions, from getting lost to finding an exciting new route to running into people you know on their own quixotic quest to get anywhere.
Second, it makes each intersection less like the others, and disrupting uniformity makes for a better sense of place. No question if I was at 3rd and 11th or 4th and 15th; the odd diagonal streets and little squares and T-intersections of olde Boston Towne (and thus modern Boston metro) are each unique and thus potentially memorable should something of interest happen.
Of course, part of my own memory of Boston is just that, my own. But I nevertheless propose that its unique (for America--a point for a different day) urban design is significant to how those memories form and how they cluster. No one would say a grid system with car travel is inherently unmemorable. But I would suggest it is differently memorable, with memories clustering more closely on destinations rather than along the way.
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