Aug 31 -
Sept. 1, 2019
Labor Day

on the grounds of the Levitt Pavilion & The Westport Library

2019 LINE UP

We are so excited about this year’s lineup. Plenty of old favorites and some new acts that will blow your mind.

Make sure you get to see all these great acts in person! Purchase your Levitt Live tickets now and save money off the gate.

Click here to see the schedule of performers for both days.

Sat., Aug. 31

Anders Osborne (with full band!)

We got on board with Anders early, first booking him for our festival in 2011, and he has since become one of the leading stars in the international roots music pantheon.  Swedish-born, New Orleans-based Anders Osborne is widely regarded as a musical triple threat: an award-winning songwriter and guitarist, he is also a singer whose raw, emotional delivery informs everything he plays.  Named the Crescent City’s Best Guitarist for the third year in a row, and the city’s Best Songwriter for the second straight year, Osborne also won Song of The Year for his composition, “Louisiana Gold”.   Longtime festival goers here have marveled at Anders’ omnivorous approach to blues/funk/Americana and beyond, or as Jambase Magazine put it:  “Osborne finds a striking balance of muscle and grace that allows for the smaller moments of quiet to be just as resounding as the sonic booms.”  Expect both from this major artist when he hits the Levitt Pavilion stage on August 31 . . . Artist Website | Tickets

Neville Jacobs   

Both Ivan Neville and Cris Jacobs have graced our stage with their own bands in previous years (Dumpstaphunk and Cris Jacobs Band, respectively).  And now, New Orleans r&b royalty from the first family of NOLA funk and a proven star in the current countrified blue-eyed soul craze that’s bubbling up around the nation (i.e., Chris Stapleton, Sturgill Simpson, Ray LaMontagne) —  have joined forces to form a roots superstar band.  Outlaw swagger meets sanctified funk meets blue-eyed soul, with evocative, heartfelt songwriting thrown in for good measure.  Neville Jacobs is one of the few bands we’ve heard with the sanctified confidence to burn it up preceding Anders Osborne onstage.  Expect the awesome! Artist Website | Tickets

Flow Tribe   

A fast-rising indie-funk sextet, Flow Tribe came together in the wake of Hurricane Katrina to raise money and spirits for their hometown New Orleans.  Their music is high energy, genre-crossing, and flirts with various styles from funk to rock and rap; in addition, the band brings a bit of ska, along with swamp and surf elements into its leading-edge approach to modern r&b.   Flow Tribe incorporates bass, guitar, trumpet, harmonica, keyboards, washboard, drums/timbales and greased-up harmony vocals in an alternative funk universe that’s street-level yet sophisticated and houseparty-elegant.  Currently considered to be the leading Crescent City party band, we’re excited to set Flow Tribe down on the Saturday night stage to play their wildly original songs and irresistible cover versions on the banks of our own Saugatuck River.  Artist Website | Tickets

Southern Avenue  

Relix Magazine referred to this fiery Memphis-based quintet as “a deeply soulful young Memphis band that’s turning the scene on its head like . . . a boiling retro-soul primer”. 

With the compelling soulstress Tierinii Jackson on lead vocals, Southern Avenue has been making its bones on the big festival stages internationally over the past 5 years.  Jackson’s sister Tikyra’s behind-the-beat groove on drums is pure Stax/Memphis funk, her snare sound cracking with fiery authority.  Guitarist-founder Ori Naftaly has the modern virtuoso chops to anchor Southern Avenue in our current musical slip-stream, which keeps the “retro” as an anchor, while soaring with true rock ‘n roll abandon, especially on songs like the band’s exquisite cover version of the Beatles’ “Come Together”.  Artist Website | Tickets

Kat Wright    

NPR once described this Burlington, Vermont-based chanteuse as “a young Bonnie Raitt meets Amy Winehouse”.  Wright performs with an 8-piece sweet-soul unit that is ultra-sympathetic to her nuanced vocals, which are both sultry and dynamic, delicate yet powerful, gritty but highly emotive.  And as with Bonnie and Amy, soul music is the jumping off point for Kat Wright’s songs, but ultimately her music is personal and powerful, with a live show to match. Artist Website | Tickets

Jake Kulak    

Guitar ace Jake Kulak has been the pride of CT’s blues scene since he first emerged as a 13-year old phenom at local jam sessions.  Now a few years later, Jake and his trio have been nominated for New England Music Award in the “Best New Act of the Year” category, and were one of 6 bands to win the Boston House of Blues Emerging Artist” competition.  Jake has been featured onstage with heavyweights like James Montgomery and Bob Margolin, and is now a force to be reckoned with, emerging as one of the brightest lights on the New England music scene. Artist Website | Tickets

Sunday, September 1


Gracie and Clyde Lawrence are the NYC-based brother /sister duo that front this horn-laden, retro-soul-infused-with-modern-pop unit.  Gracie’s magnetic vocal/stage presence combined with Clyde’s rich nine-piece arrangements pay tribute to Motown, Muscle Shoals and everything in between.  On tour nationally this summer with Jon Bellion, Lawrence is a band on the cusp, burning it up onstage.  Artist Website | Tickets

The Main Squeeze 

From their origins as at party band at Indiana University in Bloomington, The Main Squeeze has evolved into a serious LA-based funk/rock/jam band comer, now opening on tours for George Clinton, The Roots, Umphrey’s McGee, and Mac Miller.  Corey Frye’s soulful lead vocals blend with high energy funk grooves and ripping solos “that will leave you freshly squozen!” Artist Website | Tickets

High & Mighty Brass Band  

What can we say?  They played our festival in 2016 and tore the roof off the sucker!  Since then, this 9-piece brass gorilla-with-rhythm section has collaborated onstage and in the studio with such as Galactic, DJ Logic, and Eli ‘Paperboy’ Reed.  Fusing R&B, hip hop, Afro-beat and New Orleans-style funk, HMBB is very loud and very proud, and a guaranteed party for all concerned, onstage and onsite! Artist Website |Tickets

The Commonheart 

A 10-piece rock ‘n soul band based in Pittsburgh, influenced by the classics and in a league with current roots music leaders Tedeschi Trucks Band and Nathaniel Rateliff & The Night Sweats – The Commonheart’s leader/singer Clinton Clegg is a real force of nature, and this band is just beginning to break out majorly via appearances at Mountain Jam, Telluride, World Café . . . and our own Blues & Views Fest at The Levitt! Artist Website | Tickets

The National Reserve    

Singer-guitarist Sean Walsh honed this roots-rock/Americana powerhouse quartet by playing marathon weekly gigs at a bar in Williamsburg, Brooklyn, then taking it on he road for several years.  Steeped in the traditions of The Band, Dylan, NOLA funk, classic r&b and Laurel Canyon lyricism, The National Reserve has grown into a strong new limb of the classic rock family tree. Artist Website |Tickets

School of Rock   

Always a show-stopper, the renowned, Fairfield-based School of Rock fields a truly ear-boggling group of local student rockers in a band that brings down the house each and every year, performing from the classic rock canon (Allman Bros., Beatles, Stones, Muddy Waters, Janis Joplin, etc.) Artist Website | Tickets