Middlebury House of Jazz Festival Debuts in Vermont Featuring Star-Studded Lineup

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Festival will showcase internationally celebrated and rising jazz artists across the Great American Songbook, contemporary jazz, Latin and Afro-Caribbean rhythms, blues a

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Town Hall Theater and Jazz Middlebury will launch the inaugural Middlebury House of Jazz Festival, October 9–11, 2026, a three-day celebration of extraordinary musicianship, creativity, education, and community in downtown Middlebury.

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Featuring GRAMMY Award-winning artists, internationally acclaimed performers, rising stars, educational opportunities and intimate live performances, the new festival brings together an extraordinary range of jazz—from the Great American Songbook and contemporary jazz to Latin, Afro-Caribbean, blues, funk and global influences. Performances will take place in Town Hall Theater's 150-seat cabaret-style Rothrock Mainstage and intimate 75-seat Anderson Studio.

'This festival is about experiencing exceptional jazz up close,' said Lisa Mitchell, Executive & Artistic Director of Town Hall Theater. 'We want audiences to hear internationally celebrated artists in an intimate setting, discover emerging talent, meet musicians, learn from them, and experience the extraordinary range and joy of jazz over one weekend.'

'There is a huge appetite for jazz in the Middlebury community. The festival's array of talent will serve up a gourmet meal. Dig in,' said Gary Sarachan of Jazz Middlebury.

Friday, October 9 at 7:30 PM | Rothrock Mainstage

GRAMMY Award-winning producer, guitarist and vocalist John Pizzarelli opens the festival with Dear Mr. Bennett, a loving tribute to the legendary Tony Bennett and more than six decades of extraordinary music.

From early hits including 'Because of You' and 'Rags to Riches' to 'I Left My Heart in San Francisco' and Bennett's celebrated collaborations with Bill Evans , the John Pizzarelli Trio brings these iconic songs to life while Pizzarelli shares personal stories about the man behind the music.

Hailed by the Boston Globe for 'reinvigorating the Great American Songbook and re-popularizing jazz,' Pizzarelli is one of today's leading interpreters of the American Songbook. He won a GRAMMY as co-producer of James Taylor 's American Standard and has performed and recorded with artists ranging from Natalie Cole and Rosemary Clooney to Paul McCartney and James Taylor .

Tickets: $65 Table | $55 Balcony | $45 Riser

Premium seating included with VIP Festival Pass.

Saturday, October 11 at 2 PM | Anderson Studio

Acclaimed multi-instrumentalist, composer and educator Miles Donahue brings decades of adventurous, genre-crossing jazz to an intimate afternoon performance. Equally at home on trumpet, saxophone and keyboards, Donahue has performed and recorded with artists including Jerry Bergonzi, Joe Lovano, Kenny Werner and Mike Stern.

The Miles Donahue Quartet moves effortlessly among jazz standards, bebop classics, original compositions and contemporary favorites, celebrating the heart of jazz: improvisation, musical conversation and the joy of musicians responding to one another in the moment.

Tickets: $25 General | $10 Student | Included with VIP Festival Pass

Saturday, October 10 at 7:30 PM | Rothrock Mainstage

Praised as a 'rising star' by Jazzwise, French-Malagasy pianist and composer Mathis Picard blends jazz, classical traditions and global influences in an exhilarating mix of original music and imaginative interpretations of Ellington, Monk, Bach, Chopin and Ravel.

Arriving in Middlebury fresh from a featured performance at Lincoln Center the night before, Picard has collaborated with luminaries including Wynton Marsalis , Ron Carter, Christian McBride , Cécile McLorin Salvant and André De Shields . He has performed internationally from Hong Kong and Seoul to Paris and New York, and has been named Musical Director and Arranger for the revival of the Tony Award-winning Broadway musical Ain't Misbehavin'.

Tickets: $50 Table | $40 Balcony | $30 Riser

Premium seating included with VIP Festival Pass.

Saturday, October 10 | Post-show | Jean's Place Lounge

Festival VIP Passholders are invited to an intimate after-show gathering with Mathis Picard . Enjoy drinks and sweet bites, mingle with Picard, and toast an extraordinary evening of jazz. Exclusive to VIP Passholders.

Sunday, October 11 at 11 AM | Rothrock Mainstage

Picard, who began playing piano at age three, leads an interactive exploration of music, creativity and the connection between artistic expression and well-being. Beginning as a lecture and evolving into a group conversation, the class explores how caring for mind, body and spirit can nurture a richer creative life.

Tickets: $25 General | $15 Student | Included with VIP Festival Pass

Sunday, October 11 at 4 PM | Anderson Studio

Soulful vocals meet jazz, blues, Latin rhythms, funk and American roots influences in an intimate afternoon performance from fast-rising guitarist and vocalist Lara Cwass, a student of acclaimed trumpeter Ray Vega.

Born and raised in Queens and now based in Burlington, Cwass has shared stages with members of the Allman Brothers family as well as Eric Krasno, Luther Dickinson, Mike Gordon and John Medeski. The Lara Cwass Band brings together Cwass, Paul Lyons , Jack McChesney and Evan Barker for original music that is soulful, spontaneous, sweet and gritty.

Tickets: $20 General | $10 Student | Included with VIP Festival Pass

Sunday, October 11 at 7:30 PM | Rothrock Mainstage

GRAMMY Award-winning trumpeter Ray Vega leads his Afro-Caribbean Ensemble in an electrifying festival finale blending Latin jazz, Afro-Caribbean rhythms, salsa, bebop and funk.

A native of the South Bronx, Vega has performed and recorded with jazz and Latin legends including Tito Puente , Ray Barretto, Mongo Santamaria, Celia Cruz, Paquito D'Rivera, Arturo Sandoval and Eddie Palmieri, and appeared on Puente's GRAMMY-winning Mambo Birdland.

Now based in Vermont and a respected educator at the University of Vermont, Vega brings that extraordinary musical lineage to an ensemble known for fiery improvisation, irresistible grooves and a contemporary Nuyorican perspective. His career has taken him from the Blue Note and Birdland to major jazz festivals around the world—a joyful and fitting finale to the inaugural Middlebury House of Jazz Festival.

Tickets: $50 Table | $40 Balcony | $30 Riser

Premium seating included with VIP Festival Pass.

A limited number of just 48 inaugural VIP Festival Passes will offer the fullest House of Jazz experience.

$225 Early Bird/THT Member | $250 Regular (Valued at $320)

VIP Passes include:

A three-show bundle will also be available, offering a 10% discount when purchasing tickets to three festival performances.

With just 150 seats in the Rothrock Mainstage cabaret configuration and 75 seats in the Anderson Studio, audiences are encouraged to purchase tickets and passes early.

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_Originally reported by [BroadwayWorld](https://www.broadwayworld.com/vermont/article/MIDDLEBURY-HOUSE-OF-JAZZ-FESTIVAL-to-Debut-in-Vermont-20260910)._