*****Warning: Contains Many Spoilers******
Story is set entirely in a sleepy and quintessentially quaint little New England town. Autumn leaves and amber light. An unknown character arrives in town - untidy, rough, wild looking. His first encounter with the locals occurs in an art supply store. We begin to learn a little about this guy - he's British, he's an artist who only does pencil sketch portraits and his name is Colin.
Colin checks into the Battlefield Inn Motel, meeting Joanie and (later), Fisher, the couple who run the place. Joanie digs for more details and we learn that Colin has had some kind of very difficult break-up from his lady friend in Britain (Vera). Through Joanie, Colin meets Mandy - she will become his new interest. Colin and Mandy hit it off and begin spending time together. She starts lining up interesting looking characters for him to draw. This process takes us through a variety of locations. The relationship grows and becomes more serious.
Vera arrives on the scene unannounced. Colin and Mandy are in his room at the motel and Joanie is able to distract Vera long enough so that Colin and Mandy finish their business and leave without Vera seeing them (they are unaware that she's there).
Meanwhile the do-gooders over at the Chamber of Commerce have built a monument commemorating the town's origin. It's no secret the monument looks like a huge erect penis. Neckties and other assorted memorabilia have been created incorporating this image. They bring Colin in to the Chamber office for a consult and to see if he can paint a portrait of the current chamber president.
Vera finally catches up with Colin at his motel room later this evening. The encounter is awkward. We learn a little more of what has transpired she dumped him for someone else in order to inspire him to finally marry her but the plan backfired and she ended up with the other guy.
We cut to Mandy working at her job at the Shining Shores Rest Home. Colin tells Mandy that Vera has arrived. Later over dinner, they discuss writing a letter to Vera. The next day Mandy and Vera run into each other in the parking lot of the local supermarket. Vera drops hints that Colin is very ill and that she's been sleeping with him too. Mandy gives Colin the cold shoulder for a while. Colin meets with Vera again at a golf course (they walk the fairways but don't play). Colin politely tells Vera to go home. This development is then followed by scenes of general angst on both sides what to do, what to do? Both parties talk to everyone else but each other.
Later Colin goes by Mandy's apartment yet another time and buzzes. This time she agrees to talk to him. Colin senses that Vera has stirred things up between himself and Mandy. Colin denies any involvement with Vera but Mandy's not buying it. She sends him packing dejected.
Later still, Vera and Colin have connected again over coffee and apple pie. Vera has a theory that by an amazing coincidence the towns founders are her ancestors. The chamber of commerce president has convinced her to remain in town and to enter the upcoming Queen of New Cardiff contest. At the Town Square on the big day we learn that Joanie and Mandy have also entered. The contest is obviously rigged in Vera's favour and she wins the Queen of New Cardiff crown. At the big poolside wind-up B.B.Q. later there is talk that Colin has just up and left town.
We learn that Colin has a cousin touring in the US and that they'd arranged to meet at the monument. Fade to the town monument (the giant penis). Mandy and Joanie have gone to meet the cousin since Colin has supposedly left town. Colin impersonates his cousin and reconnects with Mandy. He proposes to her she faints. He carries her back to the Town Square.
Sarcastic voice over by Vera (in Tacky Queen costume) and Doug as end credits roll.