Country music superstar Kenny Chesney isn't likely to slip in and out of a restaurant in Boston without being recognized. After all, Chesney's No Shoes Nation, every bit as loyal as Deadheads to The Grateful Dead, was founded in Massachusetts, just a ways down the road at Gillette Stadium in Foxboro.

Kenny Chesney’s Boston Restaurant Appearance

Chesney didn't seem to mind drawing a crowd last Saturday at Strega North End, a legendary eatery in Boston's famed Italian North End.

Boston-based WCVB-TV 5 reported, "Guests sang along to Chesney's songs, including 'Get Along,' while the superstar soaked it all in."

Fans Sing Along With No Shoes Nation

 

Chesney posted to his Instagram account, "So you go to the restaurant in the North End of Boston for lunch, and this happens."

WCVB said Chesney posed for pictures with fans and Strega North End owner Nick Varano.

READ MORE: Kenny Chesney Shot "Knowing You" Video in This Massachusetts City

Kenneth Arnold Chesney was born in Lutrell in East Tennessee in 1968, and has sold more than 30 million albums worldwide. He has won almost every one of the major country music awards one can win.

Boston Restaurant Serves Lunch And Hospitality To Kenny Chesney
Getty Images
loading...

Chesney’s Ties to Massachusetts

Chesney has many ties to the region. A Boston Red Sox fan and good friends with New England Patriots owner Bob Kraft and his son Jonathan, Chesney has wrapped many concert tours at Gillette Stadium.

Chesney's song "Boston," one he only performs live in Massachusetts, was released January 25, 2005, on the Be As You Are album. The song is a fan favorite when Chesney serenades the faithful at Gillette Stadium.

READ MORE: How the Kenny Chesney Song "Boston" Came to Be

"I wrote that song just about some friends from the Virgin Islands," Chesney told the Boston Herald in 2010.

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

PICTURES: See Inside Kenny Chesney's Spectacular $11.5 Million Tennessee Estate

Kenny Chesney has sold his 4-bedroom, 9-bathroom, 12,599-square-foot hilltop estate in Tennessee for $11.5 million, and pictures show an opulent Mediterranean villa that is lavish even by the standards of other celebrity mansions.

Gallery Credit: Sterling Whitaker

More From WBSM-AM/AM 1420