The Richhill Agricultural, Mechanical, and Manufacturing Association (as it was called in the charter) formed July 6, 1866. There were 280 shares of stock sold to fund the fair. The first Jacksonville Fair (as it was initially named) occurred on October 3rd and 4th of that same year. The fair throughout much of the rest of the 1800s and early 1900s consisted of horse racing as the main event, and there were of course the contests that created the inevitable bragging rights of farmers, homemakers and craftsmen. Entries were taken in a large variety of categories – livestock, linen and clothing, cotton, leather, needlework, farm machinery, grains, produce, arts, furniture, flowers, bread, preserves, and even horse shoes.
Attractions in the early years included an “international circus,” balloon ascensions, fireworks, trapeze and other aerial acts, tight rope walkers, and many different bands. The first mention of rides at the fair was reported in the True Blue newspaper in 1886, stating that two large swings “did a good business.” A noteworthy story of entertainment comes from 1893. Madame and Professor Zeno were performing a balloon ascension at the fair, in which the balloon caught on fire. Madame Zeno was able to escape just in time, as the balloon was caught by the wind and blown into the side of a house about 500 yards away.
Attendance has always been more than anyone would ever expect from such a rural area. In 1879, the Wheeling Daily Intelligencer reports that, “Colonel Bridges estimates the crowd at the Jacktown Fair at between 5,000 and 6,000 people.” People from Washington County and “Little Virginia” attended even the very first fairs.
Fortunately, tragedy has only really struck once at the Jacktown Fair. In 1894, a boy named Furman Joseph Miller, 13, of Bristoria died at the fair. After the horse races finished, several boys jumped on their horses to ride on the track for fun. Furman was thrown from his horse and trampled. He sustained a severe head injury and died the next day.
In the 1920s, advertisements promote a “night fair” at Jacktown, as it was one of the earliest in the area to feature lighting. In 1939, the gas lights were replaced with electric. In 1931, the concrete road from Waynesburg to Jacktown was complete. This was great for travelers, but drastically hurt the three hotels (Bryan, Pettit, and Taylor) in Jacktown. During the fair, these hotels were bursting at the seams, often having the hire additional help for the week of the fair.
In 1932, the fair featured a wedding as the main event on Friday evening. Lawrence Ray Wood of Holbrook married Alverta McClelland of Wind Ridge in a wedding put on by Boyd and Worth of Pittsburgh. They sponsored the nuptials, paying for everything including advertisement, in exchange for a 50 percent cut of the gate proceeds. The two were happily married for the rest of their lives and relocated to California.
Throughout the 1930s and 1940s, many improvements were made to the fair under the influence of Frank Ross, a native of Wind Ridge who moved to Chicago to become the very successful owner of the Jewel Tea Company. He was a very generous man to the fair and the community. The president of the fair in the 1940s was Ross Burns, a relative of Mr. Ross, and their cooperation was vital to the development of the fair.
In 1943, it appears the fair was a small as it ever was with World War 2 at its peak. Although it seems there were no big attractions, premiums were paid for an amateur show and livestock.
Sadly, horse racing came to an end in 1946, and horse pulls became the new main event.
The 100th fair anniversary celebration in 1965 was the first five day affair and also the beginning of the tradition of the Jacktown Fair parade, along with having a fair queen.
“You can’t die happy ‘til you’ve been to the Jacktown Fair,” is first found in the Waynesburg Democrat Messenger on August 7, 1931 as “Visit Jacktown and die happy.” Though the wording has changed a few times throughout the years, current fair organizers say the adage holds true as much today as when it was first coined.
As always, the fair offers more than just rides and attractions. As stated in the Waynesburg Messenger, October 1, 1879, “If there was nothing on exhibition except the large crowd of people it would pay to spend thirty-five cents and a half day on the fair grounds. It is worth all it cost, and more too, merely as a grand reunion, and, day of recreation and social employment. We witnessed so much sociability and apparent true enjoyment, that we could not help thinking that such a day might be looked forward to as one of the most pleasant of the season, and that, if properly managed, it might be said of “fair day,” as of Christmas, “though it comes but once a year, it always brings good cheer.”