In a CMT, news-post, it was explained that the album title is derived from country music artist Radney Foster's 1992 album, Del Rio, TX 1959, which noted Foster's birthplace and birth year, as the title for this album had been for the birth year and birthplace of Rucker. Rucker said Foster's album "showed him the possibilities of country music".
The album debuted at number two on the U.S. Billboard 200, and at number one on the Top Country albums chart selling 101,000 copies in its first week of release. In its second week of release, the album dropped to number ten on the Billboard 200, selling 37,000 copies. In its third week of release, the album jumped to number nine on the Billboard 200 selling 27,000 copies. As of the chart dated July 23, 2011, the album has sold 489,681 copies in the US.
Upon its release, Charleston, SC 1966 received generally positive reviews from most music critics. At Metacritic, which assigns a normalized rating out of 100 to reviews from mainstream critics, the album received an average score of 68, based on 10 reviews, which indicates "generally favorable reviews".
Jessica Phillips with Country Weekly compared it to his previous album Learn to Live, saying "[Rucker] created a successful blend of touching love ballads and positive up-tempo meditations on life with his 2008 foray into country music, Learn to Live, and he reprises that winning mix for his sophomore country solo release", and gave it four out of five stars. Matt Bjorke with Roughstock gave it a four star rating, called all of the tracks on the record "radio ready" and said "Charleston, SC 1966 may not feature many outright old school traditional tunes like Learn to Live featured but in many ways the album features quite a few songs that show off a more 'traditional' feel than most mainstream country albums do nowadays and to be perfectly honest, it’s a sound and feel that suits Darius Rucker like a glove. Sarah Rodman with The Boston Globe favored the album over its predecessor saying it "surpasses its predecessor on the strength of more vibrant and charming tunes." Brian Mansfield with USA Today called it a "fine-sounding country album" and said that with the release, "he seems to have made his primary home in country music".
Mario Tarradell with The Dallas Morning News gave it a "B" rating, calling it a "solid follow-up" to Learn to Live, and said that he "ably captures the nuances of mainstream country".Stephen Thomas Erlewine with Allmusic calleed it "a gleaming example of polished, pressed, modern country-pop" and gave it a three star rating. Rick Moore with American Songwriter gave it three and a half stars, saying "Charleston, SC 1966 doesn’t break any rules or new ground, and probably wasn’t meant to [...] it’s obviously calculated to appeal to the million people who bought Learn to Live, so if you’re one of them, you’ll probably like this record."
Michael McCall with the Associated Press called the tracks on the release "too radio friendly" and said that "his new focus loses the creative sweep and emotional force that made his first country album so compelling. Jonathan Keefe with Slant Magazine gave it a two and a half star rating, calling the material "banal".