why does new york have a paywall around half of new england?

Given I'm a navigation nerd, I sometimes do map study. One thing that's amazing to me is how the entire southern half of New England, that being Connecticut, Massachusetts, and Rhode Island, is literally paywalled by New York.

How?

The Hudson River, that's how.

To get into Connecticut or Massachusetts from New York, you have to cross over a Hudson River bridge. This lumps in Rhode Island as well, since that's directly adjacent to the east of Connecticut.

I was experimenting with route calculations on my Garmin DriveSmart 76, and notice that on a route coming up into New England from the southwest, a toll road was used even though I specifically instructed the DriveSmart to avoid toll roads. The toll road in question was the Bear Mountain Bridge.

Error on the part of the DriveSmart? No. The DriveSmart will sometimes use a toll road if the alternative toll-free route is something so out of the way and adds so much time that it won't offer it. Fair enough.

This of course led me down a rabbit hole trying to figure out if there was any way to get into CT or MA from NY without paying a NY toll.

Nope.

Here are the bridges from south to north that "ride alongside" New England. Most of these have tolls for eastbound traffic only, which of course is the required direction to get to Connecticut or Massachusetts.

• Governor Mario M. Cuomo Bridge a.k.a. Tappan Zee Bridge, toll.
• Bear Mountain Bridge, toll.
• Newburgh-Beacon Bridge, toll.
• Mid-Hudson Bridge, toll.
• Kingston–Rhinecliff Bridge, toll.
• Rip Van Winkle Bridge, toll.
• Castleton Bridge, toll.

It is not until the Dunn Memorial Bridge where you finally get to something that's toll-free.

Where are you in relation to New England at that point? You're in Albany NY, which is due west of frickin' Adams Massachusetts at the extreme northwest corner of that state. Adams is where Mount Greylock is. Holy crap.

This means you have to go into Massachusetts using slow roads until you pick up I-91, then head south through basically the entire north-south length of MA, and then you're finally in Connecticut, starting in Enfield. Again, holy crap.

Yeah, it's no wonder the Garmin didn't offer that route as an alternative to taking Bear Mountain Bridge. Were you to look at the route on a map, the toll-free way more or less results in this giant horseshoe where you have to go north to go south just to get around New York Hudson River bridge toll roads.

New England is a giant spaghetti tangled mess of roads in cities and pretty much anywhere off-interstate. A ton of those roads used to originally be horse trails many moons ago, after all. And if you want the free way to New England, you have to deal with that mess. You're going to have to take one of those achingly slow twisty turny roads until you finally get to I-91. No way around it.

Ridiculous.

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