Henry’s family were wealthy landowners with a large plantation in the Virginia colony and a manor house in Boston. Henry’s grandfather, who was incredibly stern, had sailed to the colonies from England with his wife and young son when he was younger and had quickly built himself a life of comfort and success.

While Henry enjoyed playing with Maisie, his mother and grandparents were not approving of the friendship. His mother would often assign Maisie to do various chores in the manor if she and Henry were found together there. While his grandmother would order the poor girl around to no end, his grandfather would send the girl away, telling her to go home. 

So Henry and Maisie would usually meet outside and spend their time with outdoor games and exploring. Henry taught Maisie to read and write well. Maisie taught Henry how to do an Irish folk dance. Both learned how to ride from Mr. Jones, the head groom. Henry had Shadow, his favorite small bay gelding. Maisie preferred a slim chestnut mare named Fox. The pair would ride together and roam the woods as long and as often as possible.

The best days, however, were when Henry’s grandparents were off in Philadelphia on business and his mother was visiting her family in Boston. Then it was just Henry’s father. Henry’s father accepted Maisie as Henry’s friend and allowed the children to play together. He was a kind, gentle man who was fair to the various workers on the plantation. If anyone needed anything they would request it from him. 

To his grandparents disdain, Henry’s father was often discussing more radical ideas and would semi regularly meet with a group of men to discuss various problems the colonies had with the British crown. Henry’s father would often bring up the need for better treatment of indentured servants and slaves. 

Henry’s father did not like slavery but the plantation was home to several families of African slaves, who were purchased by Henry’s grandfather. Henry’s grandfather was very business minded and was ruthless. He would do whatever he saw fit to get the cheapest and most efficient labor. Henry was not allowed to interact much with the families and his grandparents saw that as far greater a disobedience than playing with Maisie.