For self-guided walking tour brochures, view and download here, or contact Tracy Pearce (above) or Mike Hoskins at Montgomery County History Museum, 859-498-4669, mchmky@gmail.comTake a step back in time with an historic downtown walking tour beginning at the HistoryMuseum next to the courthouse.  Downtown Mt. Sterling is full of beautifully restored buildings, churches and homes.  It also is home to the Gateway Regional Arts Center, which features exhibits in the former First United Methodist Church, which is listed in the National Register of Historic Places. Downtown events include First Friday Market, Small Town American Festival and October Court Days.The gateway between the Bluegrass and the mountains, Mt. Sterling is the county seat of Montgomery County.  It's named for an ancient burial ground called Little Mountain and for the town of Stirling, Scotland.  It was named by the first developer of the area, Hugh Forbes. The Kentucky Assembly passed an act in 1792 establishing the town as Mt. Sterling, a misspelling which was retained.In 1793 Shoe Boots (Tarsekayahke) led Cherokee and Shawnee warriors in a raid on Morgan's Station, in what was known as the last Indian raid in Kentucky. Some settlers were killed and two adolescent girls, including Clarinda Allington, were taken captive and the party returned to Cherokee territory. Believing he had saved Clarinda's life, Shoe Boots later married her, and they had three children together. He was a wealthy, successful leader. Several years later, Clarinda gained a visit back to her family in Kentucky with her children and decided to stay. They could not support her, but the state voted a 3-year pension for her.Montgomery County was established in 1796 from land given by Clark County and was the 22nd Kentucky county in order of formation. There are two theories about whom the county is named:  one in honor of Richard Montgomery, an American Revolutionary War Brigadier General killed in 1775 while attempting to capture Quebec City, Canada; the other, for Thomas Montgomery, a Virginian who served in the Revolutionary War and settled in Mt. Sterling in 1793.The area was originally part of the thick wilderness of central Kentucky. Explorers, hunters and surveyors traveling along a trail called Old Harper's Trace noted a 125-foot-high tree-covered mound which they called The Little Mountain. Later excavations showed it to be a burial site. The site of the mound is now the intersection of Queen and Locust Streets in Mt. Sterling.The first cabin in the area was built in 1779. The first permanent settlement was established around 1790, when Forbes began to sell lots and laid out a road, now Locust Street. In 1796 the town was established as the county seat of newly created Montgomery County. At that time the town consisted of 33 town lots, four retail stores, and three taverns. A courthouse was built, the first of seven to be housed in Mt. Sterling. A jail and a town pump were also installed. A large brick market house where farm produce was bought and sold confirmed the town as the commercial center of the surrounding area. Baptist, Presbyterian and Methodist churches were established during the town's first decade.During the Civil War the town was occupied alternately by Union and Confederate troops on multiple occasions. The Battle of Mt. Sterling in June 1864, which ended in a Confederate defeat, was the last of the fighting in Montgomery County.Early Mt. Sterling was the trading center for a vast part of Eastern Kentucky. It was the site of several prominent hotels, taverns, and theaters, which served as meeting places, entertainment sites, and stagecoach stops and mail depositories for post riders.  Beginning in the eighteenth century, Court Day quickly became the annual trading day for the area. It remains a big event today, held on the third Monday in October and the weekend prior. Approximately 130,000 people from all parts of the country gather for the four-day event that specializes in many different arts and crafts, food and music.

Mt. Sterling-Montgomery County Tourism

Montgomery