Mr. Winfield is a moral person, and the girls in O'Hara's story are implicated in a conspiracy against him.
The only relation Winfield wants from Farnsworth is that of a friend. When he arrives at his old home for Thanksgiving, he is filled with sorrow. Every characteristic about the house is "absolutely strange to him" (O'Hara 5), including the names near the telephone. He assumes there is "an altogether different crowd of people coming up here these days" (3). This, coupled with the fact that "it [has been] fifteen years since he [has] been up here in the summertime" (4), saddens and depresses the already melancholy Winfield. As he relaxes in his former room, "old thoughts [come] to him" (5) and he sinks further into his sulk. It is in this state that Winfield seeks out Farnie as a possible friend. Previously, she is the only one considerate enough to "[realize] that the windows [are] open and creating a terrible draught" (3).
For this reason, Winfield tries to become further acquainted with Farnie. Contemplating whether or not to open the door, Winfield thinks to himself, "it would make a bad impression if he [starts] the friendship that way" (7). Words such as these are not used in sexually motivated situations. Thus, it is made apparent that Winfield is only looking for a friend in Farnsworth due to his emotional state.
Although Winfield has made some mistakes in the past, he has sufficiently redeemed himself. It is true that he had an extra marital affair, however it was a one-time affair. Winfield "didn't have the guts to divorce his wife" (6) because he cared too much for her. When he is thinking old thoughts, he is confident in calling his past actions "regrets" (O'Hara 5). Moreover, there is no proof to substantiate that he had an affair with Ula, the maid. Upon seeing her for the first time in a while, he greets her quickly and moves on. Their conversation is short and is not at all indicative of an affair. Winfield is no longer an alcoholic. After his daughter asks him nervously what he would like to drink, Winfield "[is] amused" (4). He tells her "cocoa would be fine" (4). When asked straightforwardly if he was "on the wagon" (4), he provides a clear-cut response: "Still on it. Up there with the driver" (5).
There is a conspiracy against Winfield. From the moment he meets the girls in the limousine, this is clear. Winfield, while being the eldest of all the passengers he is made to "sit on the strapontin" (1), the most uncomfortable seat in the car. This is quite disrespectful of the girls. During the ride he is treated with additional contempt as he "[understands] that he [is] not expected to contribute to the conversation" (2). If it were only disrespect, disregard, and contempt that he is treated with then it would not be a conspiracy, but other factors contribute to it. The girls know of his former alcoholism and try to tempt him by stopping at a hotel. His granddaughter suspiciously asks, "Wouldn't you like to stop here, Grandfather?" (2). It is evident that they are trying to make a mockery of Winfield.
Later on in the story, the planned humiliation crosses the line. As dinner approaches, Winfield realizes he does not have formal clothing to wear and asks his daughter if they will be dressing up. What his daughter says is stated clearly and concisely: "We're not dressing" (5). Winfield thinks he mishears Farnsworth and he may be correct. From his perspective, what she said "sounded more like 'Come in'" (7). Winfield is under the impression that people will not be changing into different clothes. Therefore, he is very surprised when he walks into the adjoining bathroom to find Miss Farnsworth in the midst of changing. It is more than a little suspicious that Sheila, Winfield's granddaughter, had said to Farnsworth, "Remember what I told you" (O'Hara 6) only moments prior to the events in question. There is ample evidence that the girls were conspiring to humiliate Winfield.
In O'Hara's "Over the River and Through the Wood," Mr. Winfield is definitely a good-natured character. It is easy to feel for him and relate with him. He, like all humans, is not perfect. As a result, he is much easier to sympathize with. After all, it is not his past that is in question, but his present actions. When considering the present circumstances for those actions, Winfield cannot be to blame for any wrongdoing.