The Town Square is the centre of Strangetown and is where the hotel, store, saloon, City Hall and jail are located. It is one of two outdoor areas of Strangetown, the other being the Desert.

Opposite Strangetown Jail there's a cow field where cows can be milked. There's also a shed at the edge of the field which has led to much speculation as to what it does. Some people have said that when they completed the game, Honest Jackson reappears from the shed while others claim that there's a secret passage inside. These rumours are false, and the shed is just in fact a decorative object.

During game-play, the Town Square is one of four locations where Gourds and Nuclear Fuel Rods spawn. Additionally, several skillpoints appear at various points in the Town Square throughout the week.

At the start of the game, your sim's car breaks down in the Town Square, and Jebediah S. Jerky comes to their aid. The car remains in the corner by the hotel until Ava Cadavra's arrival, at which point it disappears. At the end of the game after defeating Optimum Alfred, the players's sim, dressed at the Ratticator, climbs atop the hotel's roof and the car is seen again below.