Steve Winwood’s 60-plus year career has gone through many stages: preternaturally soulful teenage singer in the Spencer Davis Group and Traffic, associate of artists like Eric Clapton, and a major solo artist with huge hits in the ’80s. He’s both a fantastic singer and a highly skilled, versatile multi-instrumentalist who’s worked as a session musician for a number of major artists, including some that might surprise you, like Miranda Lambert. In his recent appearance at Wolf Trap, his set spanned the length and wide variety of his career.
While the set was career-spanning, Winwood drew the most songs from his time with Traffic. At Wolf Trap on Sept. 20, he opened with “Glad” and played “Forty Thousand Headmen,” “The Low Spark of High Heeled Boys,” and “Dear Mr. Fantasy.” He did a couple of Spencer Davis Group numbers, playing “I’m A Man” and closing the set with “Gimme Some Lovin’.” For the cover of the Beatles’ “We Can Work It Out,” he turned vocal duties over to Nate Williams, who was accompanied by Winwood’s daughter, Lilly. Steve also did a song from his band with Eric Clapton, Blind Faith, “Can’t Find My Way Home,” and he covered Timmy Thomas’s “Why Can’t We Live Together.” He also did a few solo songs: “Roll With It,” “Back in the High Life Again,” on which he played mandolin, and “Higher Love.”
Watch the official music video for “Higher Love” by Steve Winwood on YouTube:
There’s something of a jam aspect to how Winwood likes to play. The set, which went 80 minutes, consisted of a dozen songs, and the band was given plenty of time on each to spread out and explore. Winwood himself played organ, keys, and mandolin.
I hate to have to say anything bad about a show, but the flashing lights were very intense and distracting. They made it hard to look at the stage and at times, detracting from the quality of the show.
Benmont Tench, who played keys in Tom Petty & The Heartbreakers, opened the show with a 45-minute solo set. Most of his set consisted of his solo work, including “Today I Took Your Picture Down,” “Under the Starlight,” “Pledge,” and “I Will Follow You Down.” He quipped that the Orion mentioned in the title cut from this year’s The Melancholy Season is the constellation, “not an Irish priest.” “You Should Be So Lucky,” he explained, is from the point-of-view of a woman who is being pestered by an obnoxious guy who won’t take no for answer.
Watch Benmont Tench perform “You Should Be So Lucky” live on YouTube:
His covers of Joy Division’s “Love Will Tear Us Apart” and the Velvet Underground’s “Rock & Roll” were unexpected. The two covers of Petty material, “Welcome to Hell” and “American Girl,” weren’t surprising, but they were much appreciated.
And that’s a pretty good way to describe this evening: There may not have been a lot of surprises, but it gave the fans what they wanted and sent them home happy.
Here are some photos of Steve Winwood performing live at The Filene Center at Wolf Trap on Sept. 20, 2025. All pictures copyright and courtesy of James Todd Miller.
And here are some photos of Benmont Tench opening Steve Winwood at Wolf Trap!
