This document traces four generations of a family in Marlborough, Massachusetts and how the town has changed over time. It describes how Marlborough was once known for its shoe manufacturing industry in the early 1900s when the author's great-grandmother lived there. However, most of those shoe companies are now gone and the town is filled with technology businesses. The document proposes creating an Instagram account called "Marlborough: Then and Now" to showcase pictures comparing places in Marlborough from the past to the present day in order to engage younger generations.