Tot befriended Dot Freeland, the daughter of the estate's owner. She was a year or two older, but there were no other children around and they got along very well. One day while picnicking near the river, they found an abandoned boat and quite by accident found themselves floating away in it. The current carried them through a long tunnel and after a nap they emerged in the enchanted country of Merryland.
The Watch-Dog of Merryland tried to prevent them from entering the kingdom, but the children could not propel their boat back up the river, so they ignored his orders. They passed through the first three valleys, and in the Valley of Dolls met the Queen of Merryland. She was unhappy that they had disobeyed her command that strangers were not to enter her kingdom, but she understood that it was not their fault. The Queen considered transforming the children into dolls so they could stay without incident, but ultimately decided to adopt them, making Tot a Prince of Merryland.
The Queen then accompanied the children through the last three valleys. Tot enjoyed dinner with Mrs. Tabby in the Valley of Pussycats and they spent the night in the Sixth Valley. In Valley of Lost Things, Tot found Jane, his long lost doll, and was allowed to take it with him, since it was no longer lost.
As they prepared to leave the last valley, Tot began to miss his mother and wanted to go home. The Queen, not wanting anyone in her kingdom to be sad, allowed the children to leave. They floated through the final tunnel and soon found themselves back home at Roselawn. (Dot and Tot of Merryland)