Yorkville in September

April through October gives you the full Yorkville experience. The patios open in late April, and Cumberland Street becomes an outdoor dining room. Summer brings the Yorkville Murals Festival in August and outdoor concerts in June. Fall colors peak in early October along the tree-lined streets. Winter isn't terrible — the underground PATH keeps you warm, and the holiday decorations look expensive enough to match the neighborhood. But you'll miss the outdoor energy that makes Yorkville special. Spring can be unpredictable; I've seen snow in April and 25°C weather in March.