Big Machine Records was still in its infancy upon the release of the lead single "Tim McGraw" in June 2006, and Swift and her mother helped "stuff the CD singles into envelopes to send to radio."^[46] She spent much of 2006 promoting Taylor Swift in a radio tour and later commented, "Radio tours for most artists last six weeks. Mine lasted six months."^[19] Swift baked cookies and painted canvases to gift to radio station programmers who played her music.^[47] She made many television appearances, including on the Grand Ole Opry,^[48] Good Morning America,^[49] and TRL.^[50] Swift, a self-described "kid of the internet," used Myspace to build a fanbase.^[51] This was, at the time, "revolutionary in country music."^[52] Borchetta has said that his decision to sign a sixteen-year-old singer-songwriter initially raised eyebrows among his record industry peers but Swift tapped into a previously unknown market: teenage girls who listen to country music.^[52] Following "Tim McGraw", four further singles were released throughout 2007 and 2008: "Teardrops on My Guitar", "Our Song", "Picture to Burn" and "Should've Said No". All were highly successful on the Billboard Hot Country Songs chart, with "Our Song" and "Should've Said No" both reaching number one. "Our Song" made Swift the youngest person to single-handedly write and sing a number one country song.^[53] "Teardrops on My Guitar" became a minor pop hit; it reached number thirteen on the Billboard Hot 100.^[54] The album sold 39,000 copies during its first week of release^[55] and, as of March 2011, has sold over 5.5 million copies worldwide.^[56] Swift also released a holiday album, Sounds of the Season: The Taylor Swift Holiday Collection, in October 2007 and an EP, Beautiful Eyes, in July 2008.^[57][58]

Swift toured extensively in support of Taylor Swift. In addition to her own material, Swift played covers of songs by Beyoncé, Rihanna, John Waite,Lynyrd Skynyrd and Eminem.^[59][60][61] She conducted meet-and-greet sessions with fans before and after her concerts; these lasted for up to four hours.^[62] As well as festival and theater dates, Swift performed as an opening act for several country artists' concert tours. In late 2006, she opened forRascal Flatts on the final nine dates of their Me & My Gang Tour, after the previous supporting act Eric Church was fired.^[49] Swift later sent Church her first gold record with a note: "Thanks for playing 'too long' and 'too loud' on the Flatts tour. I sincerely appreciate it. Taylor."^[63] In 2007, she served as the opening act on twenty dates for George Strait's tour,^[64] several dates on Kenny Chesney's Flip-Flop Summer Tour,^[65] selected dates on Brad Paisley's Bonfires & Amplifiers Tour^[66] and several dates for Tim McGraw and Faith Hill's joint Soul2Soul II Tour.^[67] Swift again opened for Rascal Flatts on their Still Feels Good Tour in 2008.^[68] Swift and Alan Jackson were jointly named the Nashville Songwriters Association's Songwriter/Artist of the Year in 2007, with Swift becoming the youngest person ever to be honored with the title.^[69] She also won the Country Music Association's Horizon Award for Best New Artist,^[70] the Academy of Country Music Awards's Top New Female Vocalist award^[71] and the American Music Awards's Favorite Country Female Artist honor.^[72] She was also nominated for a 2008 Grammy Award in the category of Best New Artist, but lost to Amy Winehouse.^[73]