Chestnut Bluff, which was, before 1872, a part of Dyer County, was one of the oldest towns in West Tennessee. It was given its name by the old flat-and keel-boatmen who traveled the Forked Deer River in the early 1830's and purchased their supplies for the crews there while buying furs and hides from the trappers who lived in the river bottoms. John Hartwell Moss, who came from Middle Tennessee, established the first store at the place in 1833.

Francis (Frank) Nunn and John (Jack) Nunn, from North Carolina, were early settlers who were living in the community at that time. Some of the residents in the area in the 1840's were Cornelius Johnson and his wife, Absaley; John H. Halliburton, Eli Lucas, B. O. Watson, William Shearin and H. N. Jackson.

In the 1850's F. B. Wyse had a saddle shop in Chestnut Bluff and A. W. Brooks had a store. In 1854 John Moss sold to Dr. Isaac A. Nunn (who had married Elisabeth Moss in 1849) a lot "for and in consideration of Two Dollars and fifty cents in hand paid for the further consideration of getting the improvement of the Village of Chestnut Bluff… by having a Business House built."

In the period just after the Civil War, Chestnut Bluff was regarded as one of the best business points in the state according to size. Disaster struck in the 1870's, however; a planned railroad was re-routed away from the town and, not long afterward, the whole town burned to the ground. But it was thriving again by 1903, and had four doctors located in the area. Doctors J. h. and W. T. Nunn, had by that time, constructed a brick store building, which was occupied then by B. H. Moore, who sold dry goods, groceries and hardware. Lawson Spence and a Mr. Sullivan had a store, as did Sam Young and Tom Shouse under the name of W. A. Young and Company; Young and Shouse were also undertakers. Joe H. Brooks had a drug and variety store; William B. York, a semi-retired doctor, was the postmaster and also a druggist. A cotton gin that was owned by a stock company, with Dr. W. T. Nunn as its president, was in operation; both Z. W. York and Joe S. Spence were operating sawmills. Jno. Bailey and J. B. Palmore had a blacksmith and wood shop at the time.

Until at least 1900, mail was brought to Chestnut Bluff by boat, usually the Davy Nunn, and distributed to other points by men on horseback. It appears that the almost total demise of the town as a business center occurred as a result of the river becoming unavailable and other, more rapid methods of transportation being developed. Although there are two grocery stores in the area - Bernard Mayo's and Homer Young's - as well as a television and radio shop owned by Mr. French, the only business in operation at the site of the old town is Mrs. Luther Allen's Grocery. A part of the building in which the gin was housed is now part of a barn, and the old store buildings are becoming ruins.