It's an unusual way to phrase an idiom. The idiom that is familiar to me is "they roll up the sidewalks at [time]." It means there is no "night life," everything shuts up early at night. It is strange to hear it applied to New York, of all cities. I'm not a New Yorker but I assume and believe that New York has a vigorous night life. The usual use of the phrase would be in connection with a small town, an unsophisticated, rural town. "I grew up on in a little burg in the Midwest, where they rolled up the sidewalks at nine." The mental image in my mind is that one might imagine a long carpet being rolled out for an important occasion and then rolled back up for storage... and that as a joke, as a comical exaggeration, it is said that the town is so unsophisticated that even the sidewalks are not permanent, and they are rolled up and stored a night.

I have one more thing to say about this phrase ¨the streets rolled up after a while¨. When I look at the context, Dan and Jeff´s interpretations here don´t quite make sense to me. Instead, I think what is being referred to is changes that happened in New York city over time, such as gentrification. The context suggests that this ¨rolling up¨ is not a daily or periodic phenomenon in New York, but it was a process (simple past tense) that is now complete, meaning that New York is boring now so the speaker has moved on to a city that is more fun. Or else, the speaker has a private jet, and when the streets rolled up in New York on one particular evening, he/she flew to Las Vegas to continue partying. But if we are talking about the streets rolling up every evening, we will probably use the present tense instead of the past, for the verb ¨roll¨.

I agree with the above commenters. I've never heard this phrase before and I, too, am a native speaker. good question!!

Usually people say "Roll up the sidewalks". B means that things close down for the night in New York but in Las Vegas everything is always open.