What was Boston like before GPS?

I learned to drive in the transition era - I had Google Maps printouts, but I didn't have a GPS - in southeast CT. Not quite Boston, but old colonial roads don't make much more sense than Boston does. (A three-way split, with Lambtown Road in all three directions? sure.) I primarily knew how to get from A to B, much like you might now how to follow the main arterials from square to square, but even as a geographically-oriented person I was missing the forest for the trees. As cadetcarl mentioned a few posts above, you don't really know a street network until you know the parts oblique to your usual routes - and I didn't until I started looking at Google Maps a lot.
 
I learned mostly with a “close enough” approach to navigating the city. I learned the main drags through and near the center of town like Mass. Ave., Huntington, Boylston, Comm. Ave. Beacon St. Stuart/Kneeland, Congress, State, Tremont/Cambridge, Atlantic Ave., etc. Generally speaking, almost anywhere I was going in town was within pretty easy walking distance from one of those streets. So I’d find parking along or just off that main drag closest to my destination and walk the rest of the way. Eventually, I came to know a lot more of the secondary and side streets. But that part took time and experience (and many wrong turns).

Boston’s a hot mess, but it’s small and compact. I think newcomers are surprised at how small it can feel once you start getting an idea of how close things are to each other. So if you’re OK with parking a few minutes walk away instead of fretting over the exact lane or alley your destination is located on, it’s a lot more manageable. And getting turned around on foot is a hell of a lot more forgiving than in a car.

I also did the Mapquest thing in the early 2000s (when I learned to drive). Especially for trips to outer/unfamiliar neighborhoods. But most of my driving was based on proximity to nearest surface artery as trying to read a printed map while in traffic on crowded Financial District Streets is not advisable. Today, Waze is almost always on to help avoid backups due to accidents, closures, construction, etc. Not so much because I don’t know how to get from A to B.
 
I moved to the Boston area (Somerville) in 1987 from Nebraska! (The land of the perfect grid!) For that first summer, I would just hop in the car on Saturday or Sunday and drive with no plan or direction and get hopelessly lost. As others have said, I used the Pru or Hancock sometimes as a reference point. Anyway, I would just drive around on the weekend for hours exploring the crazy tangle of roads. I went north, south, west, and yes.......even a little east. Even today over 30 years later, I remember some of those first explorations. Every once in a while I'm going someplace unfamiliar, and I think.......hey I think I was here 30 years ago. :)
 
........to add to my post above: If you are in Nebraska and you make a wrong turn, you just go around the block. Super easy! I quickly learned that was almost impossible here. You could go for miles with no way to turn around. :)
 
I've always been a map nerd and I have pretty decent wayfinding abilities. I've always preferred to look at a map before I go somewhere and figure it out. If I use a GPS at all it's only passively for wayfinding or for finding a specific address once I'm in the neighborhood.

I think the willingness and ability to "just figure it out" is integral to navigating without GPS. More and more people have lost the "willingness" part, which leads to the widespread loss of ability.

It comes up a lot with my students (8th graders). When I was a kid in the 90s, I was always staring out the window of the car. You really learn how to wayfind when you do that day after day, especially when travelling similar routes like you do when you're in a family routine. The kids of the 10s don't look out the window. They're buried in their phones from the moment they get in the car, to the moment they get out of it and are in a new place. Many of them have no physical or spacial sense of the town they live in and how it relates to surrounding communities. I guess the kids who regularly walk and bike are developing those skills a bit more.
 
I also used to take a lot of random drives, pretty much covered most of the territory north of the Pike and out to about Mt. Wachusett, and the knowledge I thus gained I still find useful 30 years later, even with GPS to back me up. Of course, in this forum it's not surprising to find a lot of mapping and navigation nerds. :) I well remember being driven from San Jose over the mountains towards Santa Cruz, and feeling really nervous and unsettled until I found a map in the glove compartment and was able to figure out where I was.
 
Riding the T and riding buses and riding commuter rail incessantly as a kid.

My parents didn't drive. I was curious. I liked knowing where random places were. So off to Dudley Square I went on the 47 or 8.

(Note: Few white people were traveling through Dudley Square in 1989.)

(Note2: If my hypothetical 10-year-old insisted on riding transit by himself today, I'd lose my mind -- even though you could argue it's safer today.)

(Note3: One time I randomly made my way to the airport, and everyone thought I was a runaway. The ride home in a statie cruiser was ... different. I guess most kids don't spend their Christmas breaks hanging out at Logan?)

When I learned how to drive and ventured into suburbia, one of those big map books was my friends. It was also at the beginning of the Tripquest (remember that?)/Mapquest era, so technology offered some hand-holding. And it was a lot easier to justify random drives when gas was 89 cents a gallon.
 
In 86 I commuted to WIT and I got lost driving around in the South End in a winter rain storm at night. I followed the elevated on Washington Street thinking I was heading North to a downtown highway connection but ended up going down to Forest Hills and after that I can't remember where I went but eventually got back home to the burbs. The scariest part was dodging the girt columns that would show up in the middle of the road, thankfully all of them were painted with the black and yellow bridge crossing symbol. I assume, thinking about it now, those columns were most likely at Dudley and Egelston Square, but there were a few close calls.
 
Yes, driving under El tracks can be an interesting experience, especially with reduced visibility. Causeway St. used to be a complete mess to navigate, needing to know well in advance which lane would feed through the posts in the right way to position you for where you wanted to exit. I never drove under the Washington St. El, aside from some of the remnant stations which were left standing much longer than the track segments.
 
I was born here and out of necessity I learned how to get around probably the same way you learned to get around your hometown.
 
In my case, how to get around was largely passed down to me. My father delivered Pepsi for a number of years, so he had an intrinsic knowledge of metro Boston just from experience. You also got used to the main routes from riding with your parents, which gets you within a shout of most places you need to go.
 
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