Throughout the history of the Woodford County Fair, there is a vivid reflection of hard-working, fun-loving, home-loving people. For many years, the fair had the characteristics of “old home week.” Families looked forward to when they would be together with friends and neighbors at the County Fair. The Fair is where the “good times” were – and still are – for the warm, friendly people of Woodford County. And so, begins the history of the Woodford County Fair . . .

On March 24, 1892, a fair association formed and stock at $100 per share offered in the “The Versailles Fair Association.” The proposal was to capitalize the association at $20,000, purchasing grounds and build a mile track, probably kite-shaped. On April 14, 1892, W. Henry Graddy was elected President, W. Irvine Arnold, Vice President; Dave McDaniel, Secretary; and John L. Amsden, Treasurer. Serving on the Board of Directors were Van P. Nelson, Nat Stone, John Ball, Gus L. Macey, James W. Miller, J. P. Amsden, J. D. Turner, J.P. Brown and Henry Helmiller. Committees were Grounds, Building, and Stock. Sixty acres at the first curve on Big Sink Pike in the “triangle” on the right between the L.S. and R.N.I.B. railroads was purchased for $100 per acre. Each railroad had a station on the grounds. Today, Big Sink Pike voting district is still referred to as “The Fairgrounds.” Building estimates were – grandstand with 2,500 seating capacity $2,500, stables $3,000, and $1,500 for the track that was a full mile track, 70 feet wide, with well thrown-up turns. M.B. Hifner, surveyor and civil engineer, laid off and engineered the track, which had one-fourth mile in each curve, one-fourth in each stretch, one-half mile up grade and one-half mile down grade. By April 14, $9,000 of $15,000 required stock had been sold, and Tobias Gibson and Harry Gilmore were to see whether the association could utilize the charter of the old Woodford Fair Association, indicating a fair association existed earlier. Named “Versailles Fair & Trotting Association,” August 2 through 5 was set for the fair. Because of the opening of the Versailles Fair and Trotting Association, the Blue Grass Clipper, the local newspaper, was published daily on August 2, 3, 4 and 5, and the items were included in the regular weekly August 1 edition. It marked the first time that a newspaper was published daily in Midway or Woodford County.

The management had pipes laid to the grounds from the Big Spring, and by the power of the pumps of the electric light plant an abundance of water for all purposes was conveyed to the Fairgrounds every day. There were 120 horses in the stables for this first meet at the new Fairgrounds. The Association provided 1,000 feet of canvas tenting; G. H. Swinney was hired for the dining room; and, there was no liquor or games of chance on the grounds. The first day people began coming in the morning and every train was loaded. When the races began at 2 p.m., the crowd had grown to over 2,500. The next day approximately 3,500 people attended. Versailles banks closed at 1 p.m. during the fair. Events were harness horse races, mule races, and bicycle races. The first race trotted was the Woodburn Stakes for three-year-olds for a purse of $500.

In February 1894 Colonel R. P. Pepper leased the track at the Versailles Fairgrounds, one of the fastest in the state, and has removed nearly all his stock to that location.

In 1895, the midway had everything from snake charmers to games like “rings and canes,” but the fair was mainly devoted to horses and cattle. By the 1900’s, 4-H became the answer to the needs of rural boys and girls. In March 1911, the Gray Lodge, Knights of Pythias of Versailles, bought the controlling interest in the Woodford County Fair Association and conducted the fair that summer. Cooperative Extension work began May 8, 1914. With all efforts directed toward winning World War II, the fair was cancelled from 1941 through 1945. The 4-H clubs had Club Day, which was held at Big Spring Park and the Court House, and the fair was cancelled. In 1946, under the direction of C. O. Neel, the Young Farmers Association revived the fair again. Concessions, 4-H, FFA, and Home Economics exhibits with food, clothing, arts & crafts, livestock, crops and more have always been mainstays of the county fair.

In 1956, the Fair was held at the old Versailles High School. The horse show was held several weeks after the fair on the old Memorial Football Field. It was later moved to the present Woodford County High School grounds. The carnival set up in the upper part of the parking lot and the cattle shows were held outside the Agriculture building. Exhibits were in the gym. The horse shows remained at the old Versailles High School until 1987 when it was moved to the present fairgrounds. The Woodford County Fair Association was incorporated July 19, 1960. The Fair was held at the Woodford County High School, Frankfort Street. No catalogs were published in 1960 or 1963.

The 1974 Woodford County Fair got under way with a parade. Contestants for fair queen, who rode in the parade, are Terri Chun, Janice Fillmore, Sissie Graves, Connie Hill, Lori Hoffmann, Tricia Nave, Diana Paul, Anne Pendleton, Deborah Redden, Jerri Smith, Vickie Smith, Katherine Tingle, Pamela Tingle, and Cathy Wehrle. Cathy Wehrle was chosen as Miss Woodford County and was selected as Miss Congeniality at the Miss Kentucky County Fair Pageant.

Due to space restrictions, the horse show was cancelled in 1977. The Fair was held at the Woodford County Middle School, Simmons Elementary, and Woodford County High School until the 1980s. A horse ring was built at the county park where the existing softball fields are located and an open horse show and 4-H horse show were held. The Woodford County Park, Simmons Elementary, and Woodford County High School were sites for the 1981 fair events.

At the October 13, 1986 Fiscal Court meeting, Clyde Johnson, Magistrate from District #2, made a motion that Fiscal Court lease 30 acres to the Woodford County Fair. The motion passed unanimously. Ray Holman was the President of the Fair Association.

For years, the fair was held in a variety of places until settling at its current location in June 1987. What was once a farm now houses two horse rings, pulling tract, horse pull track, pavilion and office building, concession stand, and asphalt parking area along with Falling Springs Recreation Center and other facilities and offices.

During the November 9, 1987 Fiscal Court meeting, Mr. Johnson, made a motion that Fiscal Court grant an additional 5 acres for the County Fair. It passed unanimously.

On January 10, 1988 the Fiscal Court granted the Fair Association the additional 5 acres behind the truck pull area.

In recent times, motor sports, pageants, and wild carnival rides have become an integral part of the fair. In June 1989, Kristi Smith was crowned Miss Woodford County Fair. Lisa Barnett was first runner-up. In 1990, the United Professional Horseman’s Association selected the Saddlebred Horse Show as the Best One-Day Horse Show and the Fair was second runner-up for the Most Progressive Fair in Kentucky. The Fair catalog received second place in the “Best Catalog” division in 1991 and “Overall Best Catalog” in 1992. The Woodford County 4-H Horse and Pony Club presented $500 to the Fair Association to begin a concession stand fund in 1994.

The first carnival, Myers International Midway, was contracted in 1996. Miss Woodford County Fair 2002, Emily Sloan, was chosen Miss Kentucky County Fair. In January 2004, Woodford County Fair Association President, George Binder, was elected President of the Kentucky Association of Fairs & Horse Shows for a one-year term. A $95,000 pavilion was built and dedicated August 13, 2004, in honor of Robert Huffman, former Woodford County Extension Agent. Kelley Fleck was the first Miss Pre-Teen Woodford County Fair and runners-up were Gina Evans, Mackenzie DeBorde, Alysha Kennedy, and Nicki Morrison. Laura Swan was crowned Miss Woodford County Fair and the runners-up were, in order, Jordan Smith, Alli Roscoe, Emma Yates and Kalyn Friddle. Miss Teen Woodford County Fair was Rebecca Devers, and runners-up were Jordan Dunn, Emily McDaniel, Tessa Mattingly, and Anne Gibson. Little Mister and Miss Woodford County Fair were Maxton Lippert and Diana Smith. In 2005, Miss Teen Woodford County Fair, Lindsay Piersawl, was chosen Miss Teen Kentucky County Fair and the Fair was selected “Most Progressive Fair Overall” in the Commonwealth of Kentucky. In 2006, Atta Tom Payton was chosen Kentucky Fair Person of the Year and the fair received an “All Kentucky County Award” and was the “Most Progressive Fair” in Zone III. Doug Estep won second place in Kentucky Demolition Derby Championship High Point Series. Mark Lancaster was President and Ken Lawson was Vice-President. The addition to Huffman Pavilion was constructed in 2006 for $247,566 and dedicated as “Payton Hall” in honor of Atta Tom Payton on September 30, 2006. The motorsports tracks received improvements totaling $19,420 in 2007 and the Fair received an “All Kentucky County Fair Award.” Brittany Wright received a college scholarship from the Kentucky Association of Fairs and Horse Shows. In 2008, the fair received the Department of Agriculture’s “Most Progressive Fair Award” in Division A, Zone III.

In January 2009, Mary Lou Watkins was elected Director of Zone III, Kentucky Association of Fairs & Horse Shows. Zone III is composed of 56 counties in the eastern 1/3 of Kentucky. New bylaws were approved for the Woodford County Fair Association and a Governing Board consisting of the Executive Board and four directors was implemented. A very wet summer caused cancellations of some Fair events and lowered the attendance somewhat. The 2009 Fair Catalog was selected “Best Catalog” in the newspaper print division during the annual Kentucky Association of Fairs and Horse Shows Convention in January 2010. The Fair also received an “All Kentucky County Award.”

In 2010, the horse shows, Kiwanis Youth Night and some motorsports events were cancelled because of rain. Attendance was approximately 17,000 patrons. The fair, once again, received an “All Kentucky County Award” from the Department of Agriculture.

The fair was awarded the Department of Agriculture’s “Most Progressive Fair in Zone III, Division A” for the year 2011. The 4-H and FFA elected to withdraw from the Fair and have an Expo in July. The theme for the 2011 fair was “The Tradition Continues”.

In 2012, the Fair received an All Kentucky County Fair Award and won the Most Progressive Fair in Zone III, Division A. Theme was “ A Treasure Chest of the County’s Best”.

The theme for the 2013 fair was “Country Things and Children’s Dreams”. Two awards were received by the Fair in 2013. An All Kentucky County Fair Award, sponsored by the Kentucky Association of Fairs and Horse Shows, and in the Department of Agriculture’s Most Progressive Fair competition, Woodford County was the runner-up in Zone III, Division A. President Mary Lou Watkins reported to the Fiscal Court that the location proposed for the carnival on the acreage behind the pulling track will not be ready for the carnival portion of the 2013 Woodford County Fair to be relocated in that area and will again be set up on the parking lot. Additionally, Woodford County did not receive the grant that was discussed previously. Lastly, the Association requested the assistance of the court in procuring "Woodford County Fairgrounds" signs. One sign would be a directional sign placed at the intersection past the second black bam indicating that left is the Fairgrounds, straight ahead are the tennis courts, and right is the football field and the back of Falling Springs Center and the last sign would be signage along US 62. Squire Dotson asked Buan Smith if he could make the signs so that all the signs would be uniform. A motion was made by Larry Craig and seconded by Jackie Brown to approve the request made to provide the signs as requested and for the signs to be made by County Engineer, Buan Smith, to create uniformity. The sign requested for the entrance of the county park on US 62 will be placed according to the recommendation made by the State Highway Department. WCFA requested the court to extend the Association's lease on the county's property. The Association is submitting an application to the Department of Agriculture for a grant, and the applicant is required to submit a ten (10) year lease ending September 30, 2023. Larry Craig made the motion and seconded by Charles "Bones" Webber to rescind the current lease and renew with a ten (10) year lease effective October 1, 2013 through September 30, 2023.

On January 8, 2014, pipes froze, burst and flooded Payton Hall. Prior to that, mold was discovered in the building. The inside was gutted, treated, cleaned and rebuilt. Contents that were salvageable were moved to the Exhibit Barn where they remained while they were treated and cleaned. What was saved was moved back in the week before the fair. In addition, a winter storm broke light poles at the pulling track and the Fair Association had to replace for $7,000+. For the first time in many years, the Fair Association was forced to seek out a new carnival due to the retirement of our long standing carnival, Myers International. The carnival selected was Miller Spectacular Shows. In February, Ruggles Sign Company donated two signs to mark the Fairgrounds. A “Woodford County Fairgrounds” sign similar to others in the park and another was added to Huffman Pavilion to designate the pavilion as the Woodford County Fair – Huffman Pavilion. At the March 24, 2014, Fiscal Court meeting Mary Lou Watkins, President, informed Fiscal Court that the Woodford County Fair Board was again not selected for a Department of Agriculture grant. The Fair Board has submitted grants since 2006 and do not plan to apply for any grants until the Department of Agriculture’s criteria of a 20-year lease can be met. The first Woodford County Fair Princess Pageant was held with Tess Thompson selected as the winner.

The theme for the 2014 fair was “Make it, Grow it, Show it! -- at the Woodford County Fair”. Rain during fair week resulted in various events being cancelled which resulted in a lower than usual attendance. After several years of not having a Saddlebred Horse Show, a very successful show, directed by Melissa Moore, was held on June 28. The fair received an “All Kentucky County Fair” award from the Department of Agriculture.

The theme for 2015 was “All Tracks Lead to the Woodford County Fair”. Fair President Mary Lou Watkins received Kentucky Fair Person of the Year Award and the WCFA received a Kentucky Department of Agriculture grant for $100,000 to construct a new Livestock Pavilion.  

The theme for 2016 was "Where Memories are made, and fun is a Tradition".  In 2016, the fair received a Kentucky Agriculture Development Board $40,000 grant from the Governor's office to complete the Livestock Pavilion.  The Woodford County Fair Livestock Pavilion was dedicated and the fair received an “All Kentucky County Fair” award.

In 2018, the fair received the All Kentucky County Fair Award and hosted the first ever amateur boxing event during the fair.

The WCFA received the All Kentucky County Fair Award for the 2019 season during the Annual Ky Fair Association Convention in January of 2020.

Due to the COVID 19 pandemic, the 2020 fair was cancelled.  Despite this, a few small events were held - pageants, the Saddlebred show, and a Disc Golf Tournament were all held.

2021 – Some Covid-19 restrictions were still in place but motorsports, livestock shows, floral exhibits, a disc golf tournament, six pageants, mule/pony pull, and a Saddlebred show were held.  Overall attendance was close to 2019.

2022 - The Fair returned to pre-pandemic activity. Jesse Whittaker was named the 2022 Kentucky County Fair Person of the Year at the annual KAFS Convention. Miss Teen Woodford County Fair, Maddie Starkey was selected as the 2023 Miss Teen Kentucky County Fair.

2023 - The Woodford County Fair was selected as the 2023 UPHA Chapter Honor Show for Chapter 9.