The little village grew as other Peters Colony settlers arrived in the area to attend brush arbor meetings of the Shiloh Cumberland Presbyterian Church, which was started by Rev.

James McNamara died in New Orleans on 5 May 1852, and his widow liquefied his assets and left Texas for the gold fields in Tuolumne County, California, with all of her remaining maternal family members.

The church was instrumental in moving Trinity University to Waxahachie in 1902 and in establishing a girls' school in the nearby town of Milford.

Ovilla continued to grow, and by the early 1900s, had a post office, a bank, a cotton gin, a pharmacy, a blacksmith shop, and several dry-goods stores.

Fires in 1918 and 1926 destroyed most of the downtown buildings, and this destruction, together with the fact that Ovilla was bypassed by railroads and major highways, led to a decline in growth.

Boxcar Willie was born in the area surrounding Ovilla; the overpass at Interstate 35E and FM 664 in Red Oak is named in his memory.

According to the United States Census Bureau, the city has a total area of 5.7 square miles (14.8 km2), all land.