Travel blog by Travels of Adam (Hipster Blog) – Travels of Adam (Hipster Blog) - Travel & Lifestyle Hipster Blog October in New York City offers a variety of romantic and fun date ideas, taking advantage of the beautiful fall weather and the city’s seasonal attractions. Fall in NYC is my absolute favorite season—the changing weather, it’s cuffing season, and the changing colors of the leaves make the city especially picturesque. Everyone has an opinion on the best month for dating, but in NYC, there’s no question: it’s when the air turns crisp and cool, but when the sun still shines.