Weston was originally the westernmost section of the Watertown settlement. The exact period when the town was first settled is unknown but is thought to have been about the mid-17th century, when land in “the Farms” was first allotted to residents. Farmers are documented to have moved to the north side of Weston by the late 17th century. In 1694, what is now Weston was set off as a separate “Farmer’s Precinct” with its own meeting house, which was located about a mile down Church Street from the Kendal Green district.
The importance of the Kendal Green area stems in part from its location at the convergence of three important roadways thought to have originated as Indian trails. North Avenue was a primary thoroughfare from Boston to New Hampshire and Vermont and then into Canada. Northern farmers used this route to drive livestock to slaughterhouses in Brighton and bring produce to Boston markets. Within the Kendal Green Historic District, North Avenue intersects with Church Street–which runs in a southwesterly direction to the Weston meeting house and town center– and with Lexington Street, which runs in a northeasterly direction to Lexington. 18th and early 19th century travelers may have stopped for refreshment at the Whitney Tavern at171 North Avenue (ca.1707-8, Map #11, MHC 18), reputed to have been built for WilliamWhitney, who married Martha Pierce of Weston in 1706. Little is known of the early history of the tavern except for a brief caption in Lamson’s History of the Town of Weston, which says that Mr. Whitney, who owned and occupied it as a tavern, once kept the famous “Punch Bowl” tavern in Brookline.