Kit was surprised and disappointed when she arrived in Connecticut, and eventually in Wethersfield. Kit had expected established towns, with solidly built buildings and paved streets. Instead, she found a much less established place when she first gazed upon Saybrook. The author described Kit's reaction:
She didn't want to admit how disappointing she found this first glimpse of America. The bleak line of shore surrounding the gray harbor was a disheartening contrast to the shimmering green and white that fringed the turquoise bay of Barbados, which was her home. The earthen wall of the fortification that faced the river was bare and ugly, and the houses beyond were no more than plain wooden boxes.
Kit had endured a long ocean journey, and had been expecting a more welcoming place. She did not feel welcomed by the "row of unimpressive shacks" in Saybrook. She had hopes for a more impressive town in Wethersfield. When she arrived, she saw that "out of the mist jutted a row of cavernous wooden structures... and beyond that the dense, dripping green of fields and woods." She did find her aunt and uncle's house to be "solid and respectable, compared to the cabins they had passed."
In Barbados, Kit had lived a life of relative freedom. She spent time outside, swam, and dressed how she pleased. Kit found her uncle in Wethersfield to be a stern and strict man. He thought that her clothes were too frivolous. She was expected to do many chores around the house and to live simply. Kit felt that her uncle did not accept her as she was. She felt like a burden at times.