One of my favorite parts of Wolf Trap’s calendar every summer are the handful of shows pairing popular music artists with the National Symphony Orchestra. These special attractions are unique shows, different from the artists’ usual presentation as a solo act or with a standard band. In Wednesday evening’s performance, singer-songwriter Gregory Alan Isakov’s moody Americana blended perfectly with the orchestra, which added elegant layers to his deeply emotional songs.
Introducing his band during the second set, after “The Fall,” Isakov noted he’s been playing with many of them for a long time. Born in Johannesburg, South Africa — where his grandfather fled to from Lithuania during WWII — and raised in Philadelphia, Gregory started touring at 16. He later moved to Colorado to study horticulture at Naropa University — he’s lived in Colorado ever since, maintaining a farm in addition to his musical career.
Watch the official music video for “The Fall” by Gregory Alan Isakov on YouTube:
Isakov began the first set with “Before the Sun,” followed by “Amsterdam” and “San Luis.” He said little over the course of the evening, but he did express how excited he was to be doing this show, and he called himself “the worst musician on this stage.” In this context, I take musician to mean instrumentalist, which may be fair — his strengths are as a songwriter and a singer. Those are aspects of musicianship, too, especially composing melodies to accompany lyrics. “Musicianship” is similar, to “athleticism,” in being vague, flexible, and sometimes misused term. (A case in point is three-time NBA MVP Nikola Jokic, who is sometimes described as unathletic because he’s not fast or explosive but excels on other physical metrics.)
The set continued with “Berth” and the title track of his fourth album, 2009’s This Empty Northern Hemisphere. Isakov rounded out the first set with “Chemicals” and the titular cut of his most recent LP, 2023’s Appaloosa Bones. (The Appaloosa is an American horse breed notable for its spotted coat pattern.) Horses feature prominently in his songs: the second set included “The Stable Song,” and he played “Feed Your Horses” in his encore. He wrapped things up with a cover of “Liars” by Ron Scott.
Following intermission, Gregory kicked off the second set with “Terlingua,” which takes its name from a town in Texas, perhaps best known for being the site of a live album by Jerry Jeff Walker. After “The Fall,” he played “Miles to Go” and “Sweet Heat Lightning.” The home stretch consisted of “Master & A Hound,” “Second Chances,” and a cover of the Lumineers’ “Caves.” After “Feed Your Horses,” he sent the audience home with “Saint Valentine.”
These orchestra concerts are always a special treat; the music is gorgeous, and it’s a welcome injection of variety. This one worked especially well: Isakov’s lyrics and melodies lend themselves to these full, luscious arrangements, with moving results.
Here are some photos of Gregory Alan Isakov performing live at Wolf Trap on August 26, 2026. All pictures copyright and courtesy of Ari Strauss.
