In 1820, Enos Doolittle arrived in Centerville, where he quickly rented a building and opened a dry goods store. Two years later, Enos married Bathsheba Robbins, the youngest daughter of one of Centerville’s founders, Benjamin Robbins.

In the same year, Enos started buying several lots of land, and in 1823 he eventually built a two-story stone building and opened the Doolittle Tavern where the current Town Hall stands. According to The History of Montgomery County, Ohio, Containing a History of the County from 1882, the Doolittle Tavern was known as the best place to stop west of the Allegheny Mountains.
The tavern also served as an inn, with sleeping quarters upstairs, and stables in the back for horses. Enos also added a large room that served as a dining room and a hall to host events and dances.

The Doolittles lived a successful and happy life, until tragedy struck:

• In May of 1835, their daughter Mary died at 15 months old
• In October 1840, their daughter Roxanna died at 16 months old
• In February of 1841, Enos suffered a debilitating stroke
• In February 1845, Bathsheba died at the age of 39
• In April 1845, their son William died at 3 months old

After all of the tragedy and loss, Enos decided to close Doolittle Tavern, and move to Columbus with his daughter Harriet. The Tavern sat neglected until it was finally torn down in 1908, and a new Town Hall was built.
Enos’s daughter Harriet wrote a letter which was read at the dedication of the new Town Hall:

“Being a child in early teens when my home was broken up, I cannot remember much of the town’s early history, yet I have with me the sweet memory of my good father’s cordial welcome to all. He was afflicted with paralysis. The unpretentious inn was known far and wide as a veritable traveler’s rest. Many celebrities among whom I remember William H. Harrison, Thomas Corwin and Henry Clay rested there. Harrison spent the night of September 9, 1840 in our home. Next morning was all bustle and excitement. It seemed everyone was going to the Whig Convention to be held in Dayton the next day. In 1843, Henry Clay with a colored servant, a novelty in Centerville at that time, spent the night with us…. I felt quite honored because I had a hearty handshake of these famous men, and very likely gloated over it childlike, you know. Before the days of the railroads, many people traveled in the private conveyances and found comfort in our simple home.”

Enos Doolittle died January 15, 1856 in Columbus, where he is also buried. The Doolittles had four daughters who did survive – Amelia, Philena, Harriet, and Eugenia.