West Springfield has changed dramatically from 1754 to the modern day. From a part of Springfield separated by a river to a city of just over 28,000 people, the area as a whole has developed tremendously.

The Day family was at the center of it all, living on one of the main thoroughfares in West Springfield. Even prior to living in the property now known as the Josiah Day House, the Day Family witnessed change for generations. Thomas Day, Josiah Day's grandfather, was one of the first settlers to receive land grants west of the Connecticut River. His children continued to live on the West Side of the River and Josiah went on to buy the Woodbridge Property in 1746. There he built the Josiah Day House.

The Day Family’s connections in West Springfield began with friendship between the Day Family and Reverend Joseph Lathrop. Reverend Lathrop, a leader within the community, spent quite a bit of time with the Day Family. However, it was not just their close friendship with the Reverend that made the Day Family prominent within the community. Throughout the years, many Day Family members held positions within town offices. Josiah Day was a co-signer on the first petition for West Springfield to become a separate town from Springfield. His son, Aaron Day, was often sought after for his advice and held several town offices himself. Even when an issue arose in the church that required advice, people turned to Aaron Day first.