BREAKING: Kenny Chesney Adds Two Shows In Massachusetts In 2027

Kenny Chesney, known for songs like 'She's Got It All,' 'How Forever Feels,' and 'She's Thinks My Tractor's Sexy,' has always embodied a cheerful summer mood. In 2027, he will perform at Gillette Stadium twice, marking his 25th appearance there, as part of the 'Original Vibe Room' tour.

If the cold weather has you feeling down, look forward to next summer. Kenny's big return after two years is nearly sold-out, with close to 400,000 tickets for the Sphere Las Vegas. He'll also bring special guests on this tour. Here's what to expect at the two stadium shows in Foxborough in 2027.

Kenny Chesney's Special Guests:

Eric Church

Sheryl Crow

Greylan James

Kenny Chesney is featuring special guests on his tour, such as country superstar Eric Church, 90s pop icon Sheryl Crow, and emerging country artist Greylan James. The tour begins in Tampa in April 2027 and includes stops at Gillette Stadium on Friday, August 27, and Saturday, August 28, 2027. If no additional shows are added afterward, these will mark the tour's final dates.

Tickets will be available to the public starting Friday, September 25th at 10:00 AM local time. Are you planning to attend the show? Let us know on our station app.

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Top 10 Kenny Chesney Songs: His Biggest Hits and Most Satisfying Deep Cuts

Kenny Chesney is a member of the Country Music Hall of Fame but it's hard to argue he's lost grip on what's hot today. This legend is definitely one of the genre's most important contemporary artists, with sold out tours and continued radio success to show off in 2026.

Here are Chesney's greatest hits. These 10 songs should top any playlist. Each one is an original. Each one is timeless.

Gallery Credit: Billy Dukes

25 Best Kenny Chesney Songs That Prove He's Country Music Hall of Fame Worthy

Kenny Chesney's best songs come from three distinct eras of his career. There are early career singles like "How Forever Feels" and mid-2000s hits like "When the Sun Goes Down," "Summertime" and "Anything But Mine."

What truly separates Chesney — a 2025 Country Music Hall of Fame inductee — from other artists is his third act. Six of the 25 songs on this list of Kenny Chesney's best were released after 2010. It's there he took some of his biggest risks, rewarding fans with some of the greatest lyrical moments and sounds of the 21st century.

We ranked the Top 25 Kenny Chesney songs using chart data, streaming and airplay numbers and staff/reader opinion. The year listed alongside the title is the year it was released as a radio single. The No. 1 song on this list exemplifies the best of what the Tennessee native is capable of.

Gallery Credit: Billy Dukes