Watch Steve Winwood and Tedeschi Trucks Band Perform a Sly Stone Medley
by Best Classic Bands Staff
Susan Tedeschi and Derek Trucks flank Steve Winwood, September 12, 2025.
Steve Winwood began his brief 2025 solo tour on September 12 with the first of two shows in which he opened for the Tedeschi Trucks Band. The seemingly ageless performer, who turned 77 on May 12, joined his hosts on stage on opening night in Bridgeport, Conn., to collaborate on a two-song medley to celebrate Sly Stone, who died earlier this year.
Six songs into the headliners’ set, Winwood was welcomed back to the Hartford HealthCare Amphitheater stage, after he had completed his own ten-song set. When the cheers subsided, the band kicked off the Family Stone medley with Susan Tedeschi singing “Sing a Simple Song” with Winwood singing the second verse. With the track winding down, longtime TTB drummer Tyler Greenwell began a solo as Derek Trucks added the stinging guitar of “I Want To Take You Higher.” Winwood later provided his own guitar solo.
On the same day as this performance, Tedeschi Trucks Band released a great concert album, Mad Dogs & Englishmen Revisited.
Related: Our 2024 Tedeschi Trucks Band concert review
Winwood’s opening set included songs from throughout his career, including Traffic (“Glad”), Blind Faith (“Can’t Find My Way Home”), the Spencer Davis Group (“Gimme Some Lovin'”) and his solo career (“Higher Love”).
Thanks to Matt Frazier for the clips.
Winwood had a backstage visitor a couple of days later.
Great seeing Steve Winwood ! @capitoltheatre pic.twitter.com/iI9p35V4aG
— Keith Richards (@officialKeef) September 19, 2025
Winwood’s tour continues through Sept. 28. Tickets are available at Ticketmaster.
In 2018, he released Winwood: Greatest Hits Live, sourced from his personal archives of live performances. The 23-song track list was handpicked by the artist and features his best-loved songs. Greatest Hits Live is Winwood’s first live release as a solo artist, spanning his lengthy career.
The collection features classic rock favorites that he made with the Spencer Davis Group (“I’m a Man,” “Gimme Some Lovin”), Traffic (“Low Spark of High Heeled Boys,” “Dear Mr. Fantasy,” among many others), Blind Faith (“Can’t Find My Way Home”), and his solo recordings (“While You See a Chance,” “Roll With It”).
Watch Winwood perform “Back in the High Life Again” from Greatest Hits Live
Related: Our review of Winwood in 2024
Steve Winwood 2025 Tour (Tickets are available at Ticketmaster and here)
Sep 19 – Red Bank, NJ – The Vogel
Sep 20 – Vienna, VA – The Filene Center at Wolf Trap (with Benmont Tench)
Sep 22 – Wilkes-Barre, PA – The F.M. Kirby Center for the Perf. Arts
Sep 24 – Morristown, NJ – Mayo PAC
Sep 26 – Atlantic City, NJ – Hard Rock Hotel & Casino Atlantic City
Sep 27 – Verona, NY – Turning Stone Resort Casino
Sep 28 – Niagara Falls, NY – OLG Stage at Fallsview Casino
Related: Listings for 100s of classic rock tours
2 Comments so far
Jump into a conversationI do so love the music that Steve Winwood has recorded over the years. There’s really been very few remarkable talents like his out there with vocals and musicianship on recordings that have transcended the years and still sound as vibrant as when they were created. But, for me, his concerts have always seemed like more or less a mail-in situation where he generally does that exact same songs as he has been doing for years in solo tours. I can remember for the longest time he toured without a bass player. I realize that Traffic generally didn’t have a bass player until late in their tenure, but, honestly, for a guy whose music is largely soulful and sometimes funky, performing with no bass player leaves a great deal lacking in the music. Never understood it, and all together as a result of this generally lackluster package of elements in his performances, in the times that I did go to his shows, I usually went home rather unsatisfied and somewhat frustrated as a result of a show with few surprises and a substandard musical presentation by one of the true greats in what should have been a memorable event.
As far as this tour with TTB and their brief onstage collaborations during their shows go, while the word “legendary” can easily be used to describe his high energy playing and singing on recordings throughout a variety of settings over the decades without any sense of hyperbole. But you can’t just step from the comfy confines of retirement in the English countryside on to the stage with a well-oiled machine like the Tedeschi-Trucks Band and not expect to be shown to have lost a step…. or two, especially at 77 years old.