The story has it that the pineapple was a "welcome" symbol for the clipper ship captains when they returned home from a voyage to their New England home port; Boston, Salem, Newport, etc. The captain would stick a pineapple on the front stair post and thereby neighbors and friends would know the captain was home.
It is cool today in New England, about 35 F so it won't be too inviting to sit outside and have a conversation.
If you do visit, make yourself comfortable amongst the archives.