After Charleston, South Carolina, in 1817, he moved to Virginia, setting up a theatrical circuit in many areas including Richmond and Petersburg.

[6] As well as managing the Camp Street Theatre for 11 years, Caldwell took his company to various towns including Natchez, Nashville, Huntsville.

There were also many other famous actors that Caldwell engaged with; Edwin Forrest was one of them who performed at the Camp Street Theatre in 1829.

Failing to get any of the citizens to join him in this pioneer, but promising, enterprise, he determined to light the city at his own expense, which remarkable feat he accomplished in September 1833.

He established gas companies in New Orleans and other cities, including Cincinnati, St. Louis and Mobile, and also prospered from real estate ventures in Louisville.