Trying to Make Sense of Poughkeepsie's Confusing Layout

One local’s musings on being Poughkeepsie bound.

Have you ever given directions to a stranger in the city of Poughkeepsie? One-ways. Roundabouts. Arterials. An east and west roadway that runs north and south around some bends. Everything you ever learned about driving gets thrown right out the car window within one city’s 31 square miles.

Here are the directions I gave to a stranger I met in the parking lot of 272 Mill Street:

Go straight around the Civic Center and make a left on red when you get to the end. Then drive up to Academy (I said in my north-south mode; if I thought of it in an east-west mindset, it would be over to Academy, wouldn’t it?)

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Turn left. Then two lights. Left on Main. Don’t worry if you miss Main Street, eventually you’ll have to turn left on another three-lane road running in the other direction. (Silently hoping they don’t notice the street name change to “Catharine.” That would take another five minutes to explain, especially since this “Catherine” believes the street name is spelled wrong.)

No, you have not made a complete circle, not yet. You can make a left on Garden from there. No, no gardens: a building, a mural, a bank, a parking lot. But do try to make the left on Main. It’s been open to car traffic again for a long, long time now.

Then, about halfway down the block, you’ll see something on the right that looks like a driveway. That’s Garden Street. Pull in there. It’s really a little cut-through that connects Garden to Main. It’s a one-way going your way — but go slow! There are these black posts that will make a nasty dent in your car if you’re not careful.

The tailor is there, in the storefront you can’t stop at. Drive right past it and pull into the parking lot on your right. Between the mural and the bank. Is that where you started? Hardly. You missed your destination by a half a block at least. You were probably distracted by this city’s old architecture as you drove. Easy to do.

Now listen, I walk this neighborhood. Every day. This really is the best way to get where you need to go. Park here and walk? Sorry, this is a private lot. Did you want directions to the parking deck instead? No, just the way home? Silly you. You might as well stay. Those directions would take too long and you are clearly now facing the wrong way.

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In this Queen City, simply don’t leave by the same route you come.


Cathy Schmitz is a resident of the Town of Poughkeepsie, but has worked for many years on Garden Street as a paralegal. When not trying to direct strangers, she volunteers for several local organizations, acts as treasurer for Arts Mid Hudson, and writes in her studio space at the newly opened Poughkeepsie Underwear Factory.

We’d love to publish your essays (maximum 550 words) about life in the Hudson Valley. Please email them to:, subject line: “The Final Word.” (All submissions become the property of Hudson Valley magazine. If published, they may be edited for clarity and space.)

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