Photo: Andrew Scott Blackstein
On Saturday evening, September 20, Greensky Bluegrass delivered their headlining sets during the Annapolis Baygrass Music Festival, held at Sandy Point State Park in Annapolis, Md. Sticking to the collective spirit of the festival’s tradition, the band welcomed all three of the event’s Artists-At-Large, including frequent collaborator, Holly Bowling, who sat in during the entire two-frame delivery, and single song participants and added guests, Kyle Tuttle and Patrick Rainey.
The band’s appearance in the Old Line State found the traditional five-piece expanding to six with Bowling’s inclusion, a decision that evoked their fan-given title, “6reensky.” The frame began with the Paul Hoffman-penned “Windshield,” before the expanded lineup pulled out one of their joint-released tunes, “Solstice,” from their shared 2024 Iceland Sessions. Next, they welcomed Tuttle to the stage, who accompanied the group on banjo during a cover of Del McCoury Band’s “My Love Will Not Change.”
Tuttle left Greensky and Bowling to wrap up their first set with another co-drop from Iceland, “Entirely Mine,” followed by setlist staple, “Run or Die.” Upon their return for the second half of their festival performance, Dave Bruzza’s fast picking, “A Letter to Seymour,” opened the frame. The group proceeded with the Hoffman-penned “In Control” before a ricochet through frequent cover “Last Winter in the Copper Country,” which rolled into “What Happened to Jim?” and in time back to Joshua Davis’ “Last Winter.”
They continued their set with takes on “Murder of Crows,” and a sequence of “Worry for You” into Handguns cut, “Don’t Lie.” For their final entry, Greensky Bluegrass used their encore to present “What You Need,” with added help from Baltimore-based saxophonist Rainey.
Prior to the arrival of the Annapolis Baygrass Music Festival, Bowling signed on to participate in Greensky Bluegrass’ 25th anniversary hometown concert on November 1, where she will serve as a guest, in addition to Lindsay Lou. Lou will also appear on the band’s October 31 performance, along with virtuoso player Sam Bush. Read more.
Scroll down to view Saturday’s setlist.
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Greensky Bluegrass
Annapolis Baygrass Music Festival
Sandy Point State Park – Annapolis, Md.
September 20, 2025
Set I: Windshield > Solstice, My Love Will Not Change1, Entirely Mine, Living Over, Run or Die
Set II: A Letter to Seymour, In Control, Last Winter in the Copper Country > What Happened to Jim? > Last Winter in the Copper Country, Murder of Crows, Worry for You > Don’t Lie
Enc.: What You Need2
Notes:
Full set with Holly Bowling
1 with Kyle Tuttle (banjo)
2 with Patrick Rainey (saxophone)
Setlist and notes via phantasytour.com.
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