The worst hill that I know in the four significant boroughs of New York City is short but still terrible. It's Miller Avenue going north from Jamaica Avenue. This is located just a little east of Broadway Junction.

There is a bike lane on southbound Miller. But they don't even bother to put one on the northbound side, evidently on the assumption that no one is going to take it. About ten years ago I decided to ride up this street. There was a guy sitting on a chair at the top of the hill; he applauded when I got to the top. (This was partly out of admiration, but partly communicating the sentiment "we don't see many fools trying that".)

There are worse hills in Fort Lee, New Jersey. I can think of one spot that is really unrideable, but is worth visiting for the unique experience.

If you go north from the George Washington Bridge on Hudson Terrace and turn left at Myrtle Avenue, you soon get to Lemoine Avenue. Just west of there is a huge drop followed immediately by an equally huge climb; the street is shaped like a U. The crazy thing is that the dip and climb are so extreme that, as you are going down the dip, you can tilt your head upward and what you see is not the sky but the road of the coming climb!

Seeing road instead of sky when you look up is disorienting, bizarre, and nothing short of surreal. Then, as you continue through the low point and up the other side, the road seems to move in front of your eyes, as it shifts from above your head down to where it belongs. It's a trippy feeling that is hard to describe.

The worst long-range hill that I have encountered was when I made the mistake of taking Eagle Rock Avenue west from West Orange, NJ to Morris County. I stupidly failed to consult a topographic map, not being in the habit of doing that.

This hill is so extreme that there are signs warning truckers of shifting loads. This is one to avoid; it made the 55-mile ride out to East Hanover more difficult that my rides to Philadelphia which were more than twice that length.