The Alcotts came into possession of the home in 1845 and named the property hillside. The Alcotts immediately began to renovate the home, which at that time was a modest structure known today as a colonial saltbox style of home. In this house, the future author Louisa May Alcott and her sisters lived out many scenes that would later shape the book Little Women. Louisa Alcott's brother, Amos Bronson Alcott opened the home to many people, and the house was even home to meetings by abolitionists and may have also sheltered fugitive slaves on their way to Canada. While most sites on the Underground Railroad are difficult to chronicle, Louisa confirmed this in her journal, saying fugitive slaves were sheltered under our roof. Bronson hoped that these experiences would teach a lesson for his family.
After the Alcott's moved out of the home in 1848, the house became the home of famed author Nathaniel Hawthorne, whose family renamed the home to what it is now known today, The Wayside. The Hawthornes called Wayside home until Nathaniel's death in 1864. The home was made open to the public in 1927 by the daughter of Margaret Sidney, who was author of the Five Little Peppers book series. Wayside became known as Home of the Authors and was made part of the Minute Man National Historical Park in 1965. The home's role in the Underground Railroad was also made official in 2001 when the National Underground Railroad Network to Freedom placed a marker on the site.