Mike Gordon and Trey Anastasio of Phish first covered “On the Road Again” during the band’s G.R.A.B. tour in 2006 and later reintroduced it into the set during their 2013 tour and again in 2017.

On Thursday, May 29, the Canadian singer-songwriter, 26, announced his upcoming On the Road Again Tour, set to celebrate 10 years since his debut album, Handwritten, later this year with dates in ...