Wearing his usual black Resistol cowboy hat, pressed Wrangler jeans, a button-down Western shirt, large silver belt buckle, and low heel cowboy boots,[1] Strait performed in the round with the eleven-member Ace in the Hole Band distributed centrally on the stage with Strait singing from each corner of the square stage in two-song segments.

[7] Strait's setlist typically consisted of a mix of his most popular recordings and performance songs, including uptempo hits like "Here for a Good Time", "Ocean Front Property", "Check Yes or No", "Marina Del Rey", "How 'Bout Them Cowgirls", "Give It Away", "Amarillo by Morning", and "Troubadour", offset by softer ballads like "I Saw God Today", "The Chair", "Living for the Night", "I Can Still Make Cheyenne", and "I'll Always Remember You".

[6] Strait's set was briefly interrupted by a ten-minute presentation given by Retired General Leroy Sisco of the Military Warriors Support Foundation to honor a wounded serviceman with the gift of a house.

At the final concert on June 7, 2014 at AT&T Stadium in Arlington, Texas, Martina McBride joined an all-star bill that included Kenny Chesney, Eric Church, Vince Gill, Faith Hill, Alan Jackson, Miranda Lambert, Lee Ann Womack, Sheryl Crow, and Asleep at the Wheel.

[10] On August 29, 2014, the Country Music Television channel broadcast a two-hour concert special of the event titled George Strait: The Cowboy Rides Away.

[12] In his review for the Austin Chronicle, Doug Freeman praised the artist's performance for the first concert of the 2014 leg of the tour, and his selection of songs that "only skim the depth of his catalog".

Though each song was delivered with a consistency that matched their familiar studio versions, his vocals remained equally sharp and subtle, whether diving low and textured on "Drinkin' Man" or smoothly drawled on "I Can Still Make Cheyenne".

[6]In his review for AZCentral, Jason P. Woodbury praised Strait's February 7, 2014 concert at the US Airways Center in Phoenix, calling his performance "an embarrassment of riches".

[1]Woodbury concluded, "He's a subtle performer, and the classic sense of regret and longing he brings to songs like 'You Look So Good in Love', 'Nobody in His Right Mind Would've Left Here', and 'A Fire I Can't Put Out' is tempered by soft humor and wit.

"[1] In his review for Billboard magazine, Thom Duffy praised Strait's March 1, 2014 performance at the Prudential Center in Newark, noting his ability to "turn musical moods at ease, as if guiding a favorite horse on a tricky trail".