Wellesley Square was originally developed in the 1850s as a crossroads between the Boston and Worcester Railroad and the Turnpike Road. The historic commercial district grew rapidly in the late 19th century, and by the early 20th century it was a thriving business center. The Square was at one time home to the Wellesley Inn (torn down to make way for the Belclare residences).
Today, Wellesley Square is a vibrant commercial center. It is home to a variety of shops, restaurants, and businesses. The square is also a popular destination for residents and visitors alike.