Lyle Lovett Brings Songs + Stories to City Winery Hudson Valley

The summer concert schedule in the Hudson Valley is always jam-packed, but few events are as anticipated as singer-songwriter Lyle Lovett’s upcoming residency at City Winery Hudson Valley.

On June 26 and 27, Lovett brings his SONGS + STORIES tour to this intimate venue in Montgomery as part of a 28-performance residency at City Winery locations in eight cities.

Lovett’s SONGS + STORIES performances blend music, conversation, and storytelling in a way only Lovett can deliver. It is a unique opportunity for new and longtime fans to experience Lovett’s wonderful songs and a lifetime’s worth of anecdotes in City Winery’s intimate listening room.

A singer, composer, and actor, Lyle Lovett has broadened the definition of American music over a career spanning 14 albums. Among his many accolades, Lovett has earned four Grammy Awards, received the Americana Music Association’s inaugural Trailblazer Award, and been named Texas State Musician. His rich, eclectic body of work remains among the most beloved in contemporary American music. 

City Winery’s multi-city residency tours reflect a return to the company’s original vision of bringing iconic artists into intimate rooms where audiences can experience music as it was meant to be – up close and deeply personal. By presenting artists for multiple nights across its nine venues nationwide, City Winery builds meaningful residencies that reach both major markets and cities where artists of this caliber might otherwise not perform in intimate settings. Recent tours have showcased music across genres, featuring artists including jazz great Jonathan Butler, R&B singer Raheem Vaughan, and Americana legend Alejandro Escovedo.

“We’re proud and a little humbled to welcome a world-class touring artist like Lyle Lovett to the Hudson Valley,” says Michael Dorf, Founder and CEO of City Winery. “It’s a tangible example of how our venue network and our position in the concert industry enable us to bring rare and special artists to this new home on the Wallkill River.”

“When Lyle and his Large Band played at City Winery in 2022, something special happened,” adds City Winery’s President of Venues, Shlomo Lipetz. “He reconnected with the magic of a small room, with the kind of connection that only happens when artists and audiences are close together. Over the years, Lyle has become part of the City Winery family, so having him return for multiple nights across all of our venues means a great deal to us and to the many music lovers who have followed him throughout his long career.”

INSIDE+OUT had the chance to catch up with Lyle by phone while he was on one of his long daily walks near his farm in Texas. Aside from a long detour into a discussion of our mutual favorite running shoes, Lovett spoke at length about his career and what we can look forward to when he visits City Winery Hudson Valley in late June.

Lyle Lovett Up Close at City Winery Hudson Valley

INSIDE+OUT: What is the concept behind these Songs + Stories shows?

Lyle Lovett: My initial interest in doing this was twofold. First, I wanted to be home a little more. With the City Winery residencies, I can do a few nights, then head back home. Also, it’s a return to my early days. It’s not a full band but a beefed-up solo show, like when I started way back, with only me and John Hagen. It’s very much a solo performance, but with someone great to play off. For the shows at City Winery Hudson Valley, I’m playing with guitarist James Harrah, a wonderful guy who has been in my Little Big Band since 2022. He’s played with everyone from Madonna and Herbie Hancock to Leonard Cohen and Ziggy Marley. 

The second is the people at the City Winery. They all really know how to take care of artists, especially their longtime programmer, Shlomo Lipetz. They came up with the concept for SONGS + STORIES, inviting me to take this stripped-down folk-singer approach across eight City Winery locations. Shlomo is a fascinating guy. In addition to his work at City Winery, he pitches for the Israeli national baseball team. I have a bobblehead of him in my home office that my kids love to play with.

INSIDE+OUT: When did you first start performing at the City Winery?

Lyle Lovett: I did four shows over six nights at the City Winery in New York City when my last album, 12th of June, was released in March 2022. I love all the rooms. The New York one is bigger than most, but they are all intimate spaces that make for a great experience for both the audience and the performer. I always feel at home at any City Winery. The idea of doing several of them and getting back to basics was hugely appealing.

INSIDE+OUT: What songs can people expect to hear?

Lyle Lovett: I’d rather not say, as I want to keep it a surprise for people. Of the three nights in St. Louis, the only songs I played every night were “If I Had A Boat” and  “12th of June.” Otherwise, I played different songs each night.

INSIDE+OUT: So, we can expect some deep cuts?

Lyle Lovett: It kind of ends up that way. I don’t do set lists; I read the room and play to it, which is the real fun of performing. I don’t generally do set lists for a band show… which makes them kind of nervous (laughs). On the rare occasions when I do, we stick to it very loosely. Beyond that, it’s very free-form. For the big band and this duo, there’s always an element of reading the audience and making a change on the fly. Everyone who works with me gets used to that pretty quickly.

INSIDE+OUT: We’ve talked about songs, so what’s the story part of the show?

Lyle Lovett: The way I do all my shows, and because of the intimacy of the room, I’m always just talking to people. It’s not like having to project to an audience in a big concert hall or amphitheater; in City Winery’s intimate rooms, it’s all very conversational.

It’s come from the folk music tradition. When I first started performing, people didn’t know me or my songs. So, I’ve always introduced songs in a way that drops enough breadcrumbs so that when the lyrics come by, they might stick a bit. I don’t do this for every song. I also talk about my past that brought me here, and my current life on the farm with my family.

INSIDE+OUT: Do you have any connections to the Hudson Valley?

Lyle Lovett: I’m excited to be back in the Hudson Valley. I’ve played here before and know many musicians who live and work here. My old manager, Gary Haber, and one of my people who helped get my career going in Nashville, Jim Rooney, helped run and build the legendary Bearsville Studio. I’m also hoping to coerce Larry Campbell and Teresa Williams into joining me at one of the City Winery Hudson Valley shows. The Hudson Valley is such a historic part of the country, a place where so much music history happened and is still happening, so yes, I love it.

INSIDE+OUT: Speaking of storytelling, is there any news on the acting front?

Lyle Lovett: Acting is never something I’ve pursued the way actors do. I don’t chase it. I have a theatrical agent, but people generally come to me, and if it feels right, I do it.

INSIDE+OUT: You were in one of my favorite comedies of all time, Walk Hard: The Dewey Cox Story.

Lyle Lovett: How great was John C. Reilly in that? He is great at whatever he does. Think of him as Dewey Cox, then as he is in Gangs of New York. He is one of our great actors and a very good singer, too.

I got involved through the director Lawrence Kasdan, the father of the film’s director, Jake Kasdan. I met Lawrence at a taping of Austin City Limits in 1997 and did a duet with Keb’ Mo‘ on a Bob Seger song in his film, Mumford. Jake called and asked me to put together a band for a scene in Dewey, so I called in all my friends, including producer Don Was, drummer Russ Kunkel’s son Nathaniel, who is one of my engineers, and a few others. It was great singing  “Walk Hard” with Jackson (Browne), Jewel, and Ghostface Killah from Wu Tang, one of the sweetest guys you could ever meet.

I really had no idea how funny this film would be or how lasting it would be. My crew and my band quote that film all the time. We say “whoopsie daisy,”  just like Dewey, whenever anything goes wrong.

INSIDE+OUT: Any new music and touring on the horizon?

Lyle Lovett:  I’m always working on songs, and when I feel I have enough to present, I make another record. After the City Winery shows, I’ll be doing 14 dates this summer with what I call my “Small Large Big Band.” I’ll be going to Alaska and Canada in September and touring the West in the fall. It’s going to be a really busy year.

I can’t believe I’ve been doing this for 50 years; it sounds crazy. It’s a real privilege. I haven’t had a real job since high school, though there are aspects of being a musician that feel like work, of course. But the music, writing songs, and then sharing them with people on record and in shows at wonderful places like the City Winery, redeems everything.

Photos by Michael Wilson + courtesy of City Winery Hudson Valley

Follow/Connect with Lyle Lovett via Website | Facebook | Instagram | YouTube | Spotify

Follow/Connect with City Winery Hudson Valley via Website | Facebook | Instagram | INSIDE+OUT Spotlight

Contributing writer Sal Cataldi is a musician, writer, and former publicist living in the Hudson Valley NY.

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