Two years ago this October, Jeff Tweedy made his Bearsville Theater debut for a three-show weekend residency. In those solo shows, Tweedy unveiled a number of then-unreleased songs from what would become the robust, three-disc, 2025 album, Twilight Overdrive. He also delighted the crowd with classic tracks from his long career leading Wilco, Uncle Tupelo, Golden Smog and Loose Fur.
The show was also a kind of landmark for the rebranded Bearsville Theater and Director of Booking for Dayglo Presents Mike Campbell. For Campbell, a huge Tweedy fan, the show was something of a dream come true. And for fans who were used to seeing Wilco in giant summer sheds, it was an opportunity to hear Tweedy up close and personal in an intimate setting.
On Monday, the prolific Tweedy returned to Woodstock for two shows with a similar formula: he used his arsenal of ancient acoustic guitars to perform twenty songs in just over an hour and a half. But now, those Twilight Overdrive songs already feel like Tweedy chestnuts. And, true to his song-a-day mantra, Tweedy is always creating something new: twenty percent of the set was committed to new and unreleased material.
Tweedy opened night one the same way he kicked off his 2024 set: with the liberating refrain of “Feel Free”, which two years later feels like essential Tweedy.
The legendary “I Am Trying to Break Your Heart” was a crowd-pleasing singalong, and scruffy Jeff could not be deterred by a stray hair that nearly derailed the Uncle Tupelo classic “New Madrid”. He wasn’t sure at first if it was a hair or a fly. Apparently at a recent show a fly stayed on his microphone all night. “I attract a series of flies,” joked Tweedy. Come for Tweedy’s music, and stay for his comedy, which often defines the singularity of any of his solo performances.
When Tweedy donned a harmonica necklace for “Via Chicago” the crowd excitedly applauded, and dry-witted Jeff asked everyone to tone it down. “[This is a] message to get people to stop applauding the harmonica,” he joked, and then told a story about how he once heard a guy play “Flight of the Bumblebee” on the mouth organ.
Bearsville shifted from comedy club to reverent folk coffee house when Tweedy played new songs, though. “Sad Ya Know” hinted at the challenges of being a supporter of someone heading for disaster (“sometimes a suicide is slow / you can see what’s coming / and it’s sad ya know”).
“Lifelong Prayer” was talkin’ country protest blues, complete with bottleneck slide guitar and Dylanesque imagist lyrics: “Keep filling my cup with beef and lemonade”. Another new track “Shady” reminded me of Arthur Rambaud Surrealism by way of a Modern Lovers single-chord groove. It kicked off with rhythmic talk-singing lines, “Let’s eat a computer / with Acid rock / I got black holes / in my socks”. A final new track, as yet untitled, made reference in under two minutes to the myth of Sisyphus, Les Paul, Isis (I’m unsure if this referenced the Islamic State, the Dylan song, or the Egyptian goddess of magic, or all three simultaneously), and Big Star’s Third.
What all of these thrilling new songs had in common was Jeff Tweedy’s current interest in eschewing traditional melody for lyrical directness and expressive poetry. The songs were as richly allusive and literary as they were rhythmically interesting, and Tweedy has seemingly moved on from his whispered vocal phase to a new fountain of Whitmanesque wordplay, delivered in plain voice. This is almost the music you expect from a songwriter who has in recent years turned into a bestselling memoirist who espouses the practice of writing a song a day for health. I’d argue he’s much more than one of our top living songwriters – he’s one of our finest poets too.
He’s a crack acoustic guitarist as well, who gets a hell of a lot out of those old Martins. “Country Song Upside-down” was accompanied by a gorgeous ringing 12-string and “Laminated Cat” was turned inside out with hints of a raga. “Airline to Heaven” was more bottleneck slide goodness. Wilco may be known for their unique production techniques and arrangements, but Jeff’s folk songs are always at the center, and his picking is as full of charisma as his stage banter.
And it wasn’t just old Martins on display. The guitar that had everybody talking (and caused one woman to commence an unsolicited Q&A) was a beautiful 1930s Kel Kroydon, completed with painted birds of paradise on the body’s flat-top. While Jeff joked that he would bore us with a history lecture, it was interesting to learn about the Gibson made guitars that were hand painted by the toy company to help keep people employed during the depression.
Despite the wooden instruments, much of the night was electric, particularly when familiar Tweedy songbook highlights elevated the experience to the level of communion. Jeff said that “Jesus, Etc.” had lost some of its spark since he has to sing it every night, so he encouraged the crowd to sing. The audience sounded like an enthusiastic choir, Tweedy the tolerant director.
While Jeff didn’t go through the theatrics of leaving the stage and returning, he told the near-sold-out crowd that the final two songs were an encore. He made sure to dedicate “I’m the Man Who Loves You” to his wife Susie, and capped off the night with “Lou Reed Was My Babysitter” a spirited punk-folk number that Tweedy wrote during the pandemic when he sincerely started to miss sweating in overcrowded rock clubs.
Tweedy returned to his role as choir director, leading the crowd into a frenzied singalong: “Cuz rock ‘n’ roll is dead, but the dead don’t die / The dead don’t die, the dead don’t die” / The dead don’t die, the dead don’t die/ Whoo!
The crowd nailed the “Whoo” the first time and Tweedy called them musical, then they totally botched it, and finally all was redeemed in a final shout of rock and roll Gestalt therapy.
It may be the Jeff Tweedy Solo Tour 2026, but as has been the case for a number of years now, Tweedy is a family affair. Jeff Tweedy’s daughter-in-law Casey Gomez Walker, son Spencer Tweedy, and grand-dog Basil were in tow for an opening set as Case Oats.
Walker featured on vocals and guitar, Spencer (usually found behind a drum kit) added harmony vocals and played guitar, and little Basil wore an adorable trick-or-treat sweater and slept in an instrument case for most of the set. Like Tweedy senior, Walker’s set featured several exciting, new, and unrecorded songs. “Haunted” was notable as it featured ringing electric guitar work from Spencer. Set closer “Closer”, which had one of the best hooks of the entire night, was also a highlight of the set.
Without the pedal steel and fiddle accoutrements that made Case Oat’s 2025 album Last Missouri Exit an atmospheric slice of alt-country, the duo’s stripped down versions of songs like “Wishing Stone” and “In a Bungalow” put Walker’s literary lyrics front and center. Walker is also one heck of a storyteller. The murder ballad “Bitter Root Lake” was my favorite track off of last year’s album and it was thrilling to hear Walker inhabit the role of Diane’s murderer in a live setting.
Despite a couple of false starts and a meddling insect (which looked like a common stink bug to me, but was labeled an “assassin bug” by a convincing audience member), Walker delivered a fine performance that brought to mind the vocals of Kim Deal (think “Drivin’ on 9”).
Spencer Tweedy’s opening set highlight was a funny story about his Woodstock hotel. As he was checking in he noticed a huge picture of Levon Helm in his room and figured he was being profiled as a drummer. No Bearsville set is complete without calling on the patron saint of Woodstock musicians, Levon Helm.
The return of all of the Tweedys to Bearsville was certainly a boost to the spirit for this Wilco-obsessive. It’s also a testament to the continued success of Dayglo Presents and their efforts to bring top caliber artists to the Catskills.
Let’s hope Jeff Tweedy and family will be back soon. Let’s hope that these new songs will be recorded, released, and will become part of the ever-growing Tweedy songbook. Let’s hope there will be more new Jeff Tweedy songs to fill the Woodstock air when we gather together again.
Jeff Tweedy – Bearsville Theater – Woodstock, NY – 10/26/26
Setlist: Feel Free; I Am Trying to Break Your Heart; Sad Ya Know (new, unreleased); New Madrid; Via Chicago; Lifelong Prayer (new, unreleased); One Sunday Morning (Song for Jane Smiley’s Boyfriend); Country Song Upside-down; Airline To Heaven; Don’t Forget; Forever Never Ends; Shady; Days Behind the Horizon (new, unreleased); Laminated Cat; Please Tell My Brother; Jesus, Etc.; Handshake Drugs; Enough; I’m the Man Who Loves You; Lou Reed Was My Babysitter
Comments are closed.