This past weekend, I rode my bike through a few parts of New York City for not a lot of time, and while I don't know if it's possible to make generalizable observations about what it *is* to ride a bike in New York (I can barely make those observations for DC, where I do have much more experience with the terrain, but mostly it's impossible to generalize because the experience of riding a bicycle is so individualistic and so varied based on all of the the social markers of who each individual is because riding a bike, unlike driving, is a much more a public act and fraught with all the perils and pitfalls of being a person in public) but I can tell you that there are parts of it that feel different and not necessarily because I wasn't totally familiar with where I was going. For the most part I knew where I was going because I had gone those places once before and not too long ago. (Also, I think New York has better signage than here. But we're always improving!) Mostly things felt different because different cities develop different norms and different ways of being and this is why I would wholeheartedly recommend taking your bike somewhere else and riding it around there some. You'll still remember how to ride your bike (after all, it's like riding a bike), but doing it somewhere different shakes some of the cobwebs brought about by familiarity and repetition, both of place and people.
tl;dr: take your bike somewhere else and ride it around there and soak up all the different feelings and notice all the differences and similarities. It's worth it, even if it's only for a few rides and not that many miles.
P.S. hot take: New York and DC are two different places and they each have good and bad things about them and comparing them is kind of silly.