Swift performed

In June 2009, Swift performed "Thug Story" with T-Pain at the CMT Music Awards. She went on to win two awards for Female Video of the Year and Video of the Year.^[64] On July 14, 2009, it was confirmed Swift would perform at the 2009 MTV Video Music Awards. "I'm so excited that MTV and the VMAs have invited me to perform, because I think this year's show will be unlike anything they've ever done!" stated Swift. "I love incorporating theatrics into my performances, and the VMAs have always allowed artists to run with that," Swift says. "MTV has been so good to me, and I could not be more excited about this year's VMAs." This was Swift's first performance on the VMAs. The show aired September 13 on MTV, with British comedian Russell Brand hosting for the second year in a row.^[65] In addition to having three of her songs featured, Swift will appear as a playable character in Band Hero.^[66] Swift announced September 6 on her MySpace blog that Fearless will be re-released on October 27 with six new songs. It will also include a DVD with her tour footage and pictures.^[67]

In January 2009, Swift announced her first headlining tour. Swift is taking her North American Fearless Tour 2009 to 52 cities in 38 states and provinces in the US and Canada over the span of 6 months. Opening acts include Kellie Pickler and Gloriana, a new group in country music. The tour features a theatrical presentation of graphics, sets and visual elements designed by Swift; Swift plays guitar as well as piano. Multiple costume changes and a fairy-tale castle are some of the elements of the three-act show.^[68]

The tour kicked off April 23 in Evansville, Indiana. On February 6, 2009, tickets went on sale for the May 22 date at Los Angeles’ Staples Center and sold out in two minutes.^[69] Tickets for several dates and venues, including Madison Square Garden, went on sale the following week and sold out in one minute.^{[70][71][72][73][74]}

On April 28, 2009, Swift gave a free, private concert to students at Bishop Ireton High School, a small Catholic school in Alexandria, Virginia after the school won a national "TXT 2 WIN" contest from Verizon Wireless.^[75] The students sent over 19,000 text messages to Verizon during a roughly one month long contest. Swift played for about an hour during the school's field day, an annual day-long recess with games and activities. On October 8, 2009 Swift's official website announced that her sold-out Fearless Tour would return to North America for 37 additional dates in 2010.