Tucker Mouse has been watching the entire conversation about the cricket, because eavesdropping on human beings is his favorite thing to do. As soon as the family leaves, Tucker jumps up onto the newsstand and tries to get the cricket's attention. The cricket introduces himself as Chester Cricket, and Tucker notes that everything he says is with a high, musical tone. Tucker introduces himself as well, and notes that he has never seen a cricket before.
The cricket says he knew quite a few mice back at his home in Connecticut. He explains that three days ago he had been practicing his jumping on a favorite tree stump when he smelled liverwurst, his favorite. Tucker interjects, running down to his stash in the drainpipe to find a bit of liverwurst to give to the cricket, who is very grateful.
He continues the story, explaining that he jumped down to go find the source of the smell and found humans having a picnic. He jumped into the basket to have a taste, but ended up eating a lot and falling asleep. Next thing he knows, someone had put a bag of sandwiches on top of him and he was stuck. At first he was not afraid, since he knew they would have to unpack the basket eventually. But as they took him to a railroad station, he got worried.
The train took him all the way to New York, and he finally got loose in the subway station and landed in the pile of dirt where Mario found him once he began to chirp. As he finishes up his story, a shadowy form leaps up and lands on the newsstand next to Chester and Tucker. Chester freaks out immediately, because it is a cat! He dives into the matchbox, not wanting to see Tucker get eaten.
But the cat does not eat Tucker. Instead, Tucker introduces the cat as his best friend, and coaxes Chester out to meet Harry Cat. Harry greets Chester warmly, and Tucker explains that cats and mice gave up being enemies in New York a long time ago, so Harry lives with him in the drain pipe. Tucker asks Chester to chirp again for Harry, and Chester makes his violin-like sound that is very pleasing to the ear.
Tucker asks if Chester will stay in New York for a while. He offers to take him to Grand Central Station to get back on a train to Connecticut, but suggests that Chester give the city a try for a little. They talk about how much Mario likes Chester Cricket, and Harry remarks that he fears for the success of the family's newsstand.
Chester is worried that he will not get along in New York, but Tucker assures him that he will be fine, and takes him up out of the subway station to see Times Square. He points out all the local sights, and Chester is amazed, but also more than a little overwhelmed. He catches sight of a star in the sky that he recognizes from back in Connecticut and is comforted to see something familiar among the new and strange.
This story is beginning to develop a prominent theme revolving around the truth that everything is not what it seems. The story itself and the characters within it are constantly surprising readers. This is a world where animals talk and think like humans, and none of these animals are what they might appear to be at first. Chester expects Harry Cat, for instance, to be vicious and eager to kill Tucker Mouse, but Harry turns out to be extremely kind and he and Tucker are best friends. The characters in this story as well as readers are constantly being surprised, because things are not always what they appear to be.
The Cricket in Times Square also relays a message about the importance of stepping outside of your comfort zone, something Chester is slowly beginning to do. He originally came to New York City against his will, forced into an uncomfortable situation. Author George Selden juxtaposes two very different places, bustling New York City and quiet suburban Connecticut, in order to show exactly how different this lifestyle is from what Chester is used to.
However, there is something to be learned from this situation, and Harry and Tucker urge Chester to stick around for a little while so that he can benefit from being outside of his comfort zone. Someone who is only ever surrounded by things that are familiar to him will never have a chance to take in new knowledge and grow as a result.
Because of this new experience, Chester will also have the chance to show how adaptable he is. Getting accustomed to something new is never easy, but Chester is slowly becoming more willing to give himself a chance to acclimate. This is shown in the final scene in Chapter 4. When Tucker takes Chester aboveground into Times Square, Chester is at first overwhelmed. However, as he gives himself time, he calms himself down and begins to adjust.
While outside, Chester spots a star he recognizes from back home in Connecticut and uses its presence to give him comfort. This star is symbolic of Chester's old life. Even though he has unwillingly left it behind to come to a world that is extremely different, his old life will never leave him completely, and it will play a role in everything he does in the present. Even if he cannot see it from down inside the subway station, that symbolic star is always there.
These chapters once again associate Chester's chirps with music. Everyone who hears his sweet sound is captivated, comparing it to rhythmic vibrations, violins, and other kinds of music. This foreshadows events to come later in the book: Chester's musical sounds will become even more important as time goes on.