I would suggest you research visiting the Hudson Valley area of New York State. Since you'll already be in West Point, you're pretty much in a good area to start your adventure. You'll find lots of apple orchards/pumpkin patches anywhere along the western shores of the river north of West Point...towns such as Highland and Modena and New Paltz come to mind. If you love hiking, I strongly suggest you park & pay for a day pass at Mohonk Mountain House in New Paltz. AMAZING trails of all abilities, and a stone tower on top of the mountain with astonishing views!! There's also the east shores of the Hudson...towns like Cold Spring, Rhinebeck, Hyde Park, Hudson, etc. Quaint towns...orchards/farms, etc. lovely vistas. If you Google "Hudson Valley tourism" you'll find lots of info for visitors.
As far as leaf colors go, we usually peak anywhere between Oct.1 and 15th, but it all depends on the weather. We got more rain than wind, so most of the trees still have leaves in place that will change over. However, exactly when they will peak is up to Mother Nature. I hope you enjoy your visit to our sublime region. I've lived here my whole life, and whenever I return home, I'm struck by the sheer beauty of the mountains, river, and farmlands.