The Old Jail Art Center (OJAC) opened in 1980 with four small galleries, in the first permanent jail built in Shackelford County. The jail was designed and built by the civil architect John Thomas of Thomas and Woerner, Builders, Fort Worth. Construction began in 1877 and was finished the following year at the cost of more than $9,000, which outraged the local taxpayers. Scottish stonemasons carved their initials into the building's large limestone blocks, in order to ensure payment for work done once the fledgling county was solvent. You can easily see why the building was known for several decades as "the alphabet jail." The "M" and the "E" are known to be the initials of stone masons named McGuire and Emery, while the "X" and the triangle are thought to be the marks of illiterate stone masons. Considered very modern at the time of its construction, the jail was used for more than half a century until it was abandoned in 1929 in favor of the "new" jail one block to the west. Robert E. Nail, Princeton graduate, local author and playwright, most notably of the Fort Griffin Fandangle, saved the building from demolition in 1940 by purchasing it for $25. He bought the lot on which it sits for $325 a few months later. One of the few outstanding examples of 19th Century Classic Architecture still in existence, the old jail building was added to the National Register of Historic Places in 1976.

Reilly Nail with an early purchase that began his art collection, ca 1950s

Reilly Nail, Princeton graduate, local author and former television producer, inherited the old jail building from his "Uncle Bobby" in 1968. A little more than a decade later, Reilly and his cousin, the artist Bill Bomar, decided to combine their collections of 20th Century modern art, and the collections of their mothers, both of whom loved Asian art. These four collections formed the core of the permanent collection, which numbers more than 2,100 art works to date. Of special interest is Jewel Nail Bomar's collection of Chinese terra-cotta tomb figures which are on permanent exhibition. The collection also includes well-known artists such as Pablo Picasso, Paul Klee, Amedeo Modigliani, Henry Moore, John Marin and Grant Wood as well as lesser-known and almost unknown artists. In addition to the permanent fine art collection, the OJAC includes Sallie Reynolds Matthews' Historical Room and Watt Matthews Ranching Collection among its many assets. The permanent collection is best described as "eclectic," even with the majority of works in it produced in the 20th Century. It contains, for example, a sizable number of works by contemporary British artists, a group not usually represented in American museums.

The Old Jail Art Center actively collects the work of young artists, and showcases young artists in its annual "Emerging Artist" exhibition. One of the underlying aims of OJAC is to encourage by both purchase and exhibition the work of young artists. Artwork in a variety of media abound both inside and out at The Old Jail Art Center. Jesús Bautista Moroles' Granite Sun anchors the Marshall R. Young Courtyard. Also located in the courtyard are Pericle Fazzini's Conversation, and several other important figurative bronze works made since 1945. The remainder of OJAC's outdoor sculpture collection is installed throughout the museum grounds. Located in front of the old jail building is another Moroles sculpture, Moon Ring 3. It was included in an invitation-only sculpture exhibition at the White House in 1995-96. Inside the museum are outstanding collections and exhibits on permanent display. The William O. Gross, Jr. Collection of Pre-Columbian Art, for example, spans several ancient cultures and some pieces date as far back as 900 B.C.

The Sallie Reynolds Matthews Room honors both its namesake, author of Interwoven and pioneer, and her youngest child and son, Watkins (Watt) Reynolds Matthews. The room is meant to be a generic family gathering room based on two rooms in the main house of Lambshead Ranch, the historic ranch of the Matthews family. In addition to its permanent exhibitions, the OJAC curates and presents temporary exhibits and hosts several traveling exhibitions.

Rapid growth necessitated additions to the museums in 1984 and 1996 with another modest addition in 2009. In 2016, a new Robert E. Nail Jr. Archives addition was opened thanks to the generosity of a local family.  All were designed by Fort Worth architect Arthur Weinman. Today the Old Jail Art Center encompasses some 17,000 square feet and is a thriving, widely-acclaimed art museum dedicated to the visual arts and to preserving the local history of the Shackelford County area. Since 1989 OJAC has been included in the select group of museums nationwide that are accredited by the American Association of Museums. Only 1 in 10 museums in the state of Texas are accredited. Serving a core audience of 25 rural counties, the Old Jail Art Center is one of the only free and accredited art museums between Fort Worth and El Paso. Because many of the local school systems do not offer any art education in their curriculum, OJAC addresses the needs of the students by providing innovative art education programs throughout the year. Adults, too, are enriched by special programming. With the 1996 addition of the Stasney Center for Education and the 2009 addition of a Distance Learning studio, OJAC now offers educational programming.