The Barn's story begins in 1756 when Josiah Smith purchased "a piece of land on the town road" for £25. By 1757, he had opened a tavern on the site which was conveniently located near the Town of Weston's meeting house. It soon became recognized as one of the most hospitable taverns on the Boston Post Road, and became the destination for people from Boston and other nearby communities for meals, dancing and playing cards.

In 1838, the tavern became known as Josiah Warren Hall, after it's owner, and it was then sold, in 1842, to the Jones brothers, whose granddaughters, Alice and Ellen Jones, kept the property intact. In the 1950's they willed the tavern to the Society for the Preservation of New England Antiquities.

After several years of using it for meetings and its primary fundraiser, The Clothing Exchange and Café, the league updated the facility so that it can be enjoyed by members of the community for meetings and social functions.

The Town of Weston now owns the building, the oldest structure in Weston Center, and leases the Barn and Connector portion of it to The Women's Community League of Weston for preservation and community use.