Small in numbers yet big in heart and soul, the intimate music, food and wine experience known as Songwriters in Paradise (SIP) returns to Healdsburg for its fifth iteration July 16-18.
To maintain a living-room atmosphere, seating is limited to between 100-150 people. Each night features at least six singer/songwriters who take turns in a round-robin style performing a song they have written, and sharing the story behind the lyrics. Multiple wines are poured throughout the evening, and hors d’oeuvres are offered to pair with them.
SIP founder Patrick Davis and his wife, Lauren Jenkins, are big fans of Healdsburg, Davis said, noting that every time he visits, he is impressed by the friendliness of the locals. He was introduced to the city by Mike Brennan, board member of the Chamber of Commerce and director of sales at Mills District, Davis said.
“What I found when I got to this quaint little Wine Country town was beauty, kindness, community and a paradise that is definitely perfect for Songwriters in Paradise,” he said.
The Musicians
The artists are all accomplished musicians, some names more familiar than others. This year’s lineup includes Davis, Jenkins, Marc Broussard, Ashley Campbell (Glen Campbell’s daughter), Thor Jensen, Kristian Bush, James Otto, Radney Foster, Levi Lowrey, Django Walker, Chris Stills (son of Stephen Stills) and Jerry Flowers, who is a SIP newcomer.
Search on those names and discover their gold-standard musical backgrounds. Bush, for example, is one-half of the acclaimed duo Sugarland, which has won multiple awards from the Grammys, Country Music Association, Academy of Country Music and Country Music and Television.
Bush said he gets song inspiration from everyday life, including eavesdropping, personal experiences or just observations. He said that while sitting in a resort lobby, he watched a tour group get off a bus and file through the lobby. As one couple separated, the woman went to the check-in desk while the man went to a large window overlooking the pool.
Excitedly the man shouted to the woman, “There’s a bar with a pool in it!” And that was the beginning of Bush’s popular song titled just that, which is on his solo EP album, Summertime Six Pack.
Lowrey, who plays multiple instruments, has shared the stage with the likes of Zac Brown Band and Mumford and Sons, and is frequently requested by fellow SIP artists to join them onstage and play his fiddle with them.
Flowers spent more than two decades playing bass with Keith Urban and writing songs for hitmakers such as Sam Hunt, Maren Morris, Jason Aldean and Morgan Wallen.
Davis has written songs with and for artists such as Guy Clark and Jimmy Buffet, and a recent release of his song “Carolina When I Die” features Darius Rucker on vocals. The song became even more relevant to Davis’ South Carolina ties when the state appointed him poet laureate.
Though SIP’s format follows a general routine, every round of every night offers a surprise. During a SIP Napa evening in 2025, for example, Stills, Bush and Davis held an impromptu guitar jam which wowed their fellow musicians and audience alike. In the most recent SIP Napa, artists trying out never-before-released songs included a performance by Otto’s 15-year-old daughter, Ava, who took the stage with Jenkins, pairing two powerhouse voices.
The Venues
Hilltop venues with Wine Country views set the scene for SIP kicking off at The Ranch at Calegari Vineyards on Westside Road on Thursday, July 16. The estate, owned by Don and Patsy Calegari, provides grapes for celebrated wineries such as Williams Selyem, one of the wineries that will be pouring wine. Other wineries featured on night one include Mauritson, Lando, Chev, Cirq Estate and Thompson 31Fifty Wines.
Bricoleur Vineyards in Windsor hosts Friday night, July 17, as estate chefs put out a spread throughout the tasting room and grounds serving savory and sweet small dishes created to complement the wines.
Robert Young Estate Winery’s sweeping vineyard views provide the backdrop for the closing night concert on Saturday, July 18. Accompanying food will be provided by the Parish Café, and other Alexander Valley wineries will share their wines as well.
Additional events are scheduled for VIP pass holders. Tickets and passes are limited and available at SongwritersInParadise.com.
