Ray LaMontagne is bringing his acclaimed debut album, Trouble, back to the stage for a special 20th anniversary celebration at Ravinia Festival in Highland Park, Illinois, on Saturday, Aug. 29.
The singer-songwriter will perform Trouble in its entirety during the concert, giving fans an opportunity to hear the album that launched his recording career two decades ago.
The concert will also feature The Weather Station, adding another singer-songwriter performance to the evening.
A Full Performance of Trouble
Released in 2004, Trouble introduced LaMontagne’s distinctive blend of folk, rock and soul-influenced songwriting to a wide audience.
The album includes several of his best-known songs, including “Trouble,” “Burn,” “Jolene” and “Shelter.” Its intimate songwriting and stripped-back sound helped establish LaMontagne as a major figure in contemporary singer-songwriter music.
For the anniversary tour, LaMontagne is revisiting the album as a complete body of work rather than simply performing a selection of individual hits.
That makes the Ravinia appearance more than a standard summer concert. It is a celebration of an album that has remained important to his career for two decades.
The Ravinia Performance
The Aug. 29 concert is scheduled for the Hunter Pavilion at Ravinia Festival, the longtime outdoor music venue in Highland Park.
The Weather Station is scheduled to perform before LaMontagne takes the stage. The project is led by Canadian singer-songwriter Tamara Lindeman and is known for its atmospheric folk songwriting.
The combination gives the evening a strong focus on songwriting and album-oriented performances.
Why the 20th Anniversary Matters
Anniversary tours have become an increasingly popular way for established artists to revisit influential albums, but LaMontagne’s decision to perform Trouble in full gives this tour a particularly clear focus.
For longtime fans, the concert offers a chance to hear the album in the same sequence as a complete performance. For newer listeners, it provides an introduction to the record that helped define LaMontagne’s early career.
The timing also gives the show a strong nostalgia factor as Trouble reaches its 20-year milestone.
A Different Kind of Ravinia Concert
Ravinia’s summer schedule features major names from across pop, rock, country, R&B and classical music. LaMontagne’s anniversary performance stands out because the centerpiece is an entire album rather than a conventional greatest-hits set.
That approach could make the Aug. 29 performance especially appealing to fans who prefer intimate songwriting and full-album experiences.
What Fans Can Expect
The concert is scheduled for Saturday, Aug. 29, at Ravinia Festival in Highland Park. The Weather Station will appear as part of the evening, followed by LaMontagne’s full performance of Trouble.
With the album reaching its 20th anniversary, the show offers fans a rare opportunity to experience one of LaMontagne’s defining records as a complete live performance.
For Ravinia, it is another major night in its 2026 summer season. For LaMontagne’s fans, it is a chance to revisit the album that started it all.