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Although the exact date when the first European stood on the Monticello Ridge and looked down on the sloping valley through the primeval forest of oaks, hickories, sweet gums, elms and maples is not known, some believe it may have been LaSalle or his lieutenant, Henry do Toni. Others, however, think that Hernando de Soto and his adventurers were the first to set foot in what is now Drew County, Arkansas.

On November 26, 1846, Drew County was formally organized and chartered and named after then Arkansas governor Thomas S. Drew, the state’s third chief executive. In 1849, early settlers Fountain and Polly Austin deeded 83 acres to establish a new county seat. Monticello was incorporated by an act of the Arkansas legislature in December 1852 and named in honor of Thomas Jefferson, whose Virginia home and estate was called Monticello. By 1850, Drew County boasted a population of more than 3,000 and by 1889; the population had grown to 15,500. Today, it is more than 18,700, with nearly 10,000 in Monticello and its outskirts.

Early settlers raised sheep and the rich delta land and fertile soil on the upland hills east of the Saline River proved prime land for growing rice, soybeans, wheat and tomatoes. In fact, Monticello was once called the “Tomato Capital of the World.” Forestry has also played a vital role in the development and continued success of Drew County. In recent years, Monticello has expanded its retail industry and has experienced phenomenal growth along Highway 425, attracting shoppers from all over Southeast Arkansas.

The area offers an abundance of leisure and recreation activities, including a new sports complex west of town, a public swimming pool, public and private golf courses, trophy bass fishing and boating on Lake Monticello, and some of the finest deer and duck hunting in the world. Monticello also boasts a six-screen movie theater, a full schedule of cultural events sponsored by the SEARK Concert Association and several local venues providing live entertainment.

Monticello is home to the University of Arkansas at Monticello, a comprehensive system of postsecondary education with its main campus in Monticello and Colleges of Technology in both Crossett and McGehee. UAM’s academic offerings range from technical certificates to traditional baccalaureate degree programs as well as master’s degrees in forestry and teacher education. Founded in 1909, UAM enrolls approximately 3,500 students.

Jordan Park in Monticello was the host for the 2008 10 Year Old Regional.