The Hamptons is a quintessential fall weekend trip that has it all: fall foliage, apple picking, pumpkin hunting, outdoor drinking and dining options that can satisfy families, couples and individuals alike. The enclave at the east end of New York’s Long Island peninsula hosts chaotic summer crowds, but things slow down considerably in early fall, making it the best time to visit this Hamptons hub. The exclusive beach town of Montauk, New York, has transformed into one of the hottest summertime escapes on the East Coast.