This is a very good question to ask, for as much as we enjoy the account of this tale and the poor hen-pecked Rip Van Winkle who is forced to escape his wife by running off to the woods and helps everybody else except his own family, some critics have argued that the way in which Rip Van Winkle goes to sleep before the American Revolution and wakes up after it suggests that this story somehow comments upon the Revolution. Such critics point towards the way in which the village is shown to have been changed by these momentous events and also how it is not actually presented as being that different after all.
Clearly, the passing of time has brought some changes, such as in the new faces and the new style of dress which Rip is not "accustomed" to. In addition, the "village was altered" in terms of its size and prosperity, having grown in both during his enchanted sleep. The presentation of the people of this village is likewise altered:
The very character of the people seemed changed. There was a busy, bustling, disputatious tone about it, instead of the accustomed phlegm and drowsy tranquility.
In particular, the men at the inn seem to be very interested in politics and talking about contemporary debates.
However, in spite of these changes, some critics argue that the emphasis is placed on how the intervening years have not actually changed the village and Rip's life. The inn has the same face on its sign, although some changes have been made to overtly alter the portrait:
The red coat was changed for one of blue and buff, a sword was held in the hand instead of a sceptre, the head was decorated with a cocked hat...
The sign says that the portrait is of "General Washington," yet the superficial changes make us question whether this historical change has actually made any lasting difference. Rip is shown to re-enter his old life very swiftly, relieved at the loss of his wife, and quickly enters the social life of the village and the inn. We are told that "the chagnes of states and empires made but little impression on him," but he is far more interested in the way in which the death of his wife impacts his life. Thus through this story Irving seems to be pointing towards the way in which the American Revolution did not actually change that much after all.