The Town of Littleton is a prime example of a colonial town built on the dismantling of a Praying Indian Town, Nashobah, founded in 1654. The adjacent area to the east was part of the “New Grant of 1655” to the Town of Concord. The southeastern section of Littleton, called Nashoba Farm and later Nashoba, was the part first settled by colonists. All settlement was abandoned during King Philip’s War. Intense competition over desirable land after the end of hostilities generated diffused settlement without a town center.

Littleton remained primarily a farming town from the seventeenth to the early twentieth century. Grazing and orchards, the principal agrarian pursuits, began in the Colonial Period. Vegetable and fruit growing became important in the early nineteenth century. Apple orchards in Littleton became renowned as among the finest in the state.