Dierks Bentley Was ‘Wondering Where’ Luke Bryan’s Shorts Were in New Post from Their 100-Mile Bike Race

by Emily Morgan

Dierks Bentley has a question for his friend and country superstar, Luke Bryan. On Sunday, the “Gone” singer took to Twitter to post a snap of the two after they competed in the Natchez Trace Century Ride.

“Not sure what was harder… doing 100 miles in 4 hours and 30 minutes or going out in public without my shorts on ha. Spent most of the time behind @LukeBryanOnline wondering where his were too,” Bentley tweeted. Instead of their typical cowboy boots and button-ups, the country singers are rocking spandex bike shorts, helmets, and sunglasses.

On Saturday, both Bryan and Bentley competed in the Jackson, Miss. cycling competition which saw more than 1,000 cyclists. During the race, Bryan and Bentley rode alongside professional cyclists such as Robbie Ventura and Christian Vande Velde.

Ventura was a member of the U.S. World Team and won more than 70 victories during his cycling career. Velde is a two-time top 10 finisher in the Tour de France. He was also a winner of the U.S.A. Pro Cycling Challenge. He’s now working as a commentator for NBC and NBCSN.

In fact, it was Ventura who encouraged Dierks Bentley and Luke Bryan to sign up, according to Wendy Bourdin, the special events coordinator for the city of Ridgeland. “Some people saw that two professional cyclists (had signed up), so those who follow cycling knew they were coming,” she said. However, she said Ventura asked that the country singer’s names be kept under wraps.

“I just didn’t tell anyone,” she said. “People were very excited when they found out they were here.”

Dierks Bentley Gets Ready to Hit the Road for Dive Bar Tour

Dierks Bentley is gearing up to play five small-venue shows in a few weeks on a brief tour titled, the High Times & Hangovers Tour. Additionally, it’s been 15 years since Bentley embarked on a tour of the same name, with the same opening act.

In 2006, Bentley played his first High Times & Hangovers Tour, with Cody Canada & the Departed opening the shows. Canada, of Cross Canadian Ragweed fame, will be touring with Bentley for his tour.

He kicks off his tour on May 11 at the Windjammer in Isle of Palms, S.C. Afterward, he’ll play four additional shows back-to-back. He then goes to Greenville, S.C.; Charlotte, N.C.; Gainesville, Fla.; and Knoxville, Tenn.

“The idea of being up onstage seems totally frightening right now, as well as, like, super exciting … That’s the way it should always feel, and it definitely feels that way right now, times 10,” Bentley confessed before the 2021 ACM Awards in mid-April. He then said he’d be announcing a dive bar tour “just for the heck of it.”