The Chowan County Fair was organized in the Spring and Summer of 1947.  It was known as the American Legion Fair for a number of years.  The first fair was held on the latter days of 1947 at the old National Guard Armory (now the Edenton-Chowan Recreation Center).  The armory was used as an exhibit building and the midway "Virginia Greater Shows" was set up in the rear of the armory.   The first fair officials were Jordan Yates, W. (Monk) Mills, Willis McClenny, and Wesley Chesson as secretary and treasurer.  Legion members served as committee members and workers of the fair.  The Chowan Agriculture Extension Service and School system were heavily involved and has continued to be to the present day.

The fair continued to be held at the armory until we began to have problems with the Town of Edenton in 1949 and 1950 over trash clean-up after the fair.  The American Legion began to look for a farm to establish a Legion home and Fairgrounds.  The Hardison Farm on US 17 South became available and was purchased by the Legion in 1950.  The fair was held at the new property in 1951, using tents to house the exhibits.  The following year1952 a fifty-by-one hundred foot concrete block building on a cement floor with rest rooms was constructed to serve as a Legion home and a fair exhibit building.

Monk mills, Jordan Yates, Willis McClenny and Roy Leary were the fair officials when we made the move to the Hardison Farm on US 17.  The fair began to grow little by little, but we had problems with carnivals that had Girl Shows and gambling on the midway.  Being a small fair and having to book small midways that carried these vices at that day and time was unavoidable.  The Legion hung in there trying to improve the fair through better exhibits and cleaner midways.  The fair continued to grow in attendance, and with the continued growth we could book larger and better midways.

In 1954 Monk Mills was manager of the fair, and William "Bill" Perry was president of the fair.  Monk Mills became ill during the week of the fair and Bill Perry took over to replace Mills who was unable to return due to heart problems.  In June 1955 William A. "Bill" Perry was elected Fair manager and held the position of Fair President or Fair Manager until the close of the 1992 fair; a total of 38 years of fair management.  Perry remained on the fair board as President Emeritus.  EC Toppin became President an Manager of the Chowan County Fair.

From the beginning, the American Legion set up the organization of the fair as follows.  The Post Commander served as the President of the Fair.  The Finance Officer of the Legion also served as Treasurer of the Fair, and the Fair Manager position was appointed to someone who was experienced and well-qualified to run the Fair.  The American Legion found this type of organization was not working well.  A large number of Post Commanders had no experience in operating a fair, and had no desire to head up the Fair.

In the 1970's the Fair was incorporated as a separate organization.  The name of the fair was changed to the Chowan County Fair.  The Fair was sponsored by, and accountable to, the American Legion.  The new fair organization elected its officers and fair board members.  The Legion required three fourths of the board members to be members of the American Legion.  This reorganization gave the Fair stability and works well.

During the seventies the Fair grew out of the one exhibit building.  The Fair bought three old mobile home house trailers, ripped the guts out, and made them into exhibit trailers.  This expansion gave us some breathing room to display a larger number of exhibits.

The Fair continued to grow in size and attendance over the years.  In 1985 the old barn was renovated to what is now called THE SHOW BARN.  This SHOW BARN was used to present livestock shows, beauty pageants, entertainment, and community use.  The SHOW BARN proved to be a big asset to the Fair.

The Fair continued to grow, and we soon found ourselves in need of more room to expand the exhibits.  Parking space was also beginning to be critical fo Fair patrons.  To solve the parking problem, the Fair made a deal with the Griffin family who owned the farm to the rear and back side of the American Legion.  In this arrangement the Legion secured ten acres of land for parking.  In 1995 the American Legion purchased the Griffin Farm, which gave the American Legion and the Chowan County fair an additional fifty-four acres of land to use for expansion.

In 1989 a new sixty by one hundred foot metal exhibit building was constructed to house exhibits and use for office space.  The Fair now has two large exhibit buildings.  These two buildings are continually being used for community functions, when not being used during Fair Week.

EC Toppin became Fair Manager and President of the Fair after the 1992 Fair.  The Chowan County Fair was reorganized to a President-Manager with two Vice-Presidents, Secretary, Treasurer, and a twelve-member Board.  This new organization seems to be working well.  It should be mentioned at this time that Earl White has served as Fair Treasurer from the 1960's until the present time.  He has done a great job for many years.

Over the years the Fair has grown from a nine or ten ride fair to a twenty-five ride fair.  Many different carnivals and shows have played at the Chowan County fair.  The Fair has won many state awards in the last twenty years, and is well known throughout the state as an excellent fair.  The Chowan County Fair has provided two State Presidents of the NC Agricultural Fair Association: William A. "Bill" Perry, and EC Toppin.  Francis Earl White also served a term on the State association.

Today the Fair presents good clean midways, excellent exhibits, and shows for the entire family.  The Chowan County Fair received the Most Improved Fair in its Category in 1996.

Since 1997, the Chowan County Fair has continued to grow, both in attendance and in entries, until in 1998 it became the Chowan County Regional Fair.  By going regional and inviting the residents of the eleven counties surrounding Chowan County to become part of the fair, entries have increased 30% and attendance has grown to more than double the population of Chowan County, to over 27,000 in 2007.

The Fair Board has continued to be active in the North Carolina Association of Agricultural Fairs (NCAOAF).  Board members have regularly attended the annual Convention and served on various committees of the NCOAOF.  The Chowan County Regional Fair recently had another of its board members serve nine years on the Board of Directors of the NCOAOF, including one term as President.  This is the fourth Chowan Board member to serve on the Association's Board and the third to serve as President.

The Chowan County Regional Fair has continued to win awards such as the Youth Award, the Agricultural Award, the Media Award (two years in a row), and in 2007, the prestigious Image Award for best medium-size fair in North Carolina.