European settlers came into the area now known as Walkertown as early as the 1750s. From 1850 through the early 20th century, the local economy was dependent on farming, lumber manufacturing, grain milling, and merchandising. Tobacco manufacturing began
early in the 19th century and became a thriving industry for the Sullivan, Booe, Poindexter, and Crews families. The Roanoke & Southern Railroad began serving Walkertown in 1889, and with it the availability of larger markets spurred the growth of industry. The Leight Lumber Company was established near the depot around 1890 and prospered by making boxes for manufacturers and lumber for construction. The Walkertown Chair Company, begun in 1903, flourished until a devastating fire destroyed most of the buildings in 1940. The Walkertown Roller Mill, built by Robah Payne around 1900, has changed hands a few times and is now the oldest continuously operating business in Walkertown.

The Chautauqua Institution was started in 1874 by the Normal Department of the Methodist Episcopal Church as a two-week program to instruct Sunday school teachers of all Protestant denominations. The program proved to be a popular combination of worship, education, and recreation and each year brought thousands of visitors to the beautiful shores of Chautauqua Lake. As Chautauqua became a model of for lifelong learning and the good use of leisure time, hundreds of similar sites were built across the continent. The Chautauqua program included lectures, classes, symphony concerts, opera, theater, art, and recreations such as golf, tennis, swimming, and sailing. In time, the movement embraced all denominations and faiths. Today Chautauqua offers a vacation filled with many opportunities in a setting that could be from a century ago.