Halloween in New York gets talked about as the Village parade, which is a fine thing to watch on television and a difficult thing to enjoy with a six-year-old on your shoulders. The version we actually send families to is at the other end of the island, at the top of Central Park, and it's free.
The Halloween Pumpkin Flotilla has been running on the Harlem Meer for more than thirty years. Kids carve or bring a pumpkin, hand it over, and at dusk the pumpkins go out on the water lit up while the crowd walks the shoreline path. There's a costume parade, crafts, and storytelling in the hours before. It's run by the Central Park Conservancy, it costs nothing, and it ends early enough that dinner is still possible.
One honest caveat on dates. The event lands in the last week of October and it moves. In 2025 it ran Thursday, October 30, 4pm to 7pm. The Conservancy publishes the current year's date on its calendar at centralparknyc.org in early fall, and it has been called off for weather before, so check the day of if the forecast is bad.
Below is what's worth doing around it, and how we'd get there from East 62nd Street.