The one I recall hitting New York was Hurricane Floyd in 1999. It hit on a Friday in mid-day and I was at work. I was doing admin work and I recall following it that morning as it hit Washington DC over the Internet on my office PC. I think I had Windows95.

Most government offices in Washington were closing down by late morning and the transit agency, WMATA, put everything it had into a very early rush hour. Then they announced they were shutting down in advance of the main part of the storm about 11AM or 12PM. I was following this over the Internet in real time. People were posting on message boards in Washington, things like, "Why am I still at work? When are they going to let us go home?" I recall one woman posting that she had been turned away by a transit bus; that by, I don't know, 12:15?, the order had gone out to the bus operators to no longer pick people up. Just drop off the riders still on board and then head back to the garages. Apparently it was starting to get pretty bad and the bus operators wanted to go home too! Anyway, she wrote that she had banged on the bus' front door but the driver wouldn't open up. He was only opening the back door to let people get off. She said she pleaded with him but he just shook his head. This happened to a number of people and it became a news item. The transit agency took a lot of heat for doing that: leaving riders at bus stops on their own during a hurricane.
I was in the Operations section of a manufacturing plant and when the office finally sent everyone home we couldn't leave until we "secured" everything. The leading edge of the storm hit around 1 PM and it was very scary. Heavy rain, high wind gusts. I guess around 2PM the eye of the storm was approaching and everything calmed down. People in my section began leaving on their own, including me. To take advantage of the calm before the trailing edge hit. It was surreal, too, when the eye was directly overhead the sun came out!
I think I got a ride home or I took the bus, in my area they may have been still running, and I made it home just as the trailing edge struck. Incredibly the local McDonald's was still open. I was in there getting coffee when the rain started again. The staff were laughing, saying they were all going to be swept away probably. I remember the asst. manager, a woman I had gotten to know pretty well (and who was friends with my wife), saying to me, "You're home early, did they let you go?" When I said yes she said, "I wish they'd let us go." She told me they were staying open, for one thing so city employees would have a place to get coffee and food.
I got in the house literally as the storm broke. Everyone else was home. Only Daddy had been been dumb enough to go to work that day. (The schools never opened.) Within minutes the winds were whipping and we had a torrential downpour. As I remember, the winds weren't as strong in the second round but the rain was much much heavier. I have never seen it rain like that. Except maybe in Vietnam during the rainy season. A deluge, Biblical. New York suffered a lot of serious flooding from Floyd.
I've been paranoid about hurricanes ever since and for some reason I don't like the feel of this one, of Irma.
