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From a motorized frame of mind, it's easy to think that roads should go everywhere you want to go. This kind of thinking prioritizes destination over journey, and that's a mistake. The journey is at least as important.
The journey is where the adventure happens, where you can be surprised and delighted. On the journey interesting things can happen that you don't expect.
From a municipal planning perspective, roads are expensive to build and maintain. Scores of snowplows and sanders are ready to go all winter long aren't cheap to keep on standby.
That's not the worst part. The more we rely on roads to carry us from place to place, the further away everything gets. The additional space the roads take up is part of this, and it also makes it easier to sprawl by making available cheap land on the outskirts of the city.
Then there's the traffic jams. If the system has trouble it can choke off access. The first level solution would suggest building more roads. That works for a while, in the same way that smoking a cigarette temporarily alleviates a smoker's craving for nicotine. They'll be back for more.
More roads attract more cars, which makes the problem bigger, not better. Building tighter, walkable communities instead will make communities thrive rather than simply being collections of houses.
There are plenty of benefits to building walkable communities. The health benefits of using walking as your primary method of getting around are significant.
For municipal governments, the cost savings of limiting road construction and maintenance can't be overlooked.
For shopkeepers, it's clear that people don't shop from their cars, they shop when they're walking. They can look in the windows and decide to come inside far more easily than they can if they're in their cars.
Building more roads solves the wrong problem. A better question is how can we create great places for people to live, work, and play without needing to strangle ourselves with roads.