For a summer baby like me who grew up in Miami and never truly experienced fall before, I definitely appreciate the seasonal festivities now that I live in Manhattan. Truly, the whole vibe of the city changes from the food to the clothes to the activities. It's quite funny because while living in Miami and the Caribbean you don't truly feel a change in seasonal activities until Christmas time hits.
With that, I recommend visiting NYC anytime during late September-late November in order to enjoy and experience all of the fall festivities.
Here are a few activities:
-strolling through Central Park (I recommend starting at Columbus Circle)
-shopping on 5th Ave (specifically in Central Park South- east side) or SOHO
-pick up a hot cocoa at Bryant Park Winter Village and The Lodge
-go on a fall foliage brunch cruise that takes you around the NY harbour
-attend a pumpkin patch on Governor's Island
-aimlessly walk through a new neighborhood (examples: Park Slope, Williamsburg, Battery Park City, Upper West Side, Astoria)
-take advantage of the seasonal goods sold at Trader Joe's