Ricky Skaggs and Sharon White

Old Town New Folk

Concert series sponsored by Blue Heaven (click here to view the full lineup →)
Ricky Skaggs and Sharon White smile warmly outdoors, each holding their instruments — Skaggs with his mandolin, White with her guitar. Sunlight filters through the trees behind them, capturing the warmth, harmony, and enduring partnership that define their decades-long musical and personal journey.

Tuesday, March 24, 7pm

Helmerich Theater

$125 front row, $85 general admission

Wednesday, March 25, 7pm

Hugh’s View

$125 front row, $95 general admission

This season of Old Town New Folk closes with an evening of bluegrass brilliance and pure harmony, as two of country music’s most celebrated voices share the stage.

Ricky Skaggs and Sharon White are a musical partnership woven from love, legacy, and more than six decades of song. Earning 12 #1 hit singles, 15 GRAMMY® Awards, 13 IBMA Awards, nine ACM Awards, eight CMA Awards (including Entertainer of the Year), along with inductions into the Bluegrass Music and Country Music Hall of Fame, Ricky Skaggs is truly a pioneer of Bluegrass and Country music. Since his beginnings in music over 60 years ago, the Grand Ole Opry member has released more than 30 albums and performed thousands of live shows with his ace backing band, Kentucky Thunder. He started his own record label, Skaggs Family Records, in 1997, releasing 12 consecutive GRAMMY®-nominated albums and has published his autobiography, “Kentucky Traveler.”

Sharon White is a member of beloved Country-Gospel family band, The Whites, and has been making music alongside her father Buck and sister Cheryl for more than five decades. They originally began as a Bluegrass group, but the family trio became well known for their string of Country hits in the 1980s, including “Hangin’ Around,” “Give Me Back That Old Familiar Feeling,” and “Pins and Needles.” The Whites are Grand Ole Opry members and were involved in the 2001 hit movie and soundtrack, O Brother, Where Art Thou? They have gone on to win GRAMMY®, CMA and Dove Awards, among others.

Joining the evening is Mike Rogers, celebrated vocalist and founding member of the acclaimed harmony group Brothers of the Heart. Formerly the lead singer of the chart-topping band BlackHawk, Rogers brings deep roots in classic country and bluegrass, adding another layer of harmony to this unforgettable night.

Old Town New Folk is underwritten by Nick and Lorie Howley, with additional support from Doug and Sherri Montgomery, John and Marilyn Rintamaki, Nell Smets, and Michael Blades and Kathy Kilroy. 

Jake Shimabukuro

Old Town New Folk

Concert series sponsored by Blue Heaven (click here to view the full lineup →)
Ukulele virtuoso Jake Shimabukuro stands against a vivid red wall, strumming his instrument with a relaxed smile. Dressed in a black leather jacket and dark shirt, he radiates calm confidence and creative energy, embodying the boundary-breaking spirit that has made him one of the world’s most celebrated ukulele players.

Tuesday, March 10, 7pm

Helmerich Theater

$125 front row, $85 general admission

Wednesday, March 11, 7pm

Hugh’s View

$125 front row, $95 general admission

Hailed as the “Jimi Hendrix of the ukulele,” Jake Shimabukuro has taken the four-string instrument to breathtaking new heights. Since first gaining worldwide fame with his viral rendition of George Harrison’s “While My Guitar Gently Weeps,” Shimabukuro has toured the globe—from the Hollywood Bowl to the Sydney Opera House—mesmerizing audiences with his lightning-fast technique and genre-defying sound.

Over the course of more than a dozen albums, the Hawaii-born musician has collaborated with an astonishing roster that includes Yo-Yo Ma, Jimmy Buffett, Bela Fleck, Bette Midler, and Willie Nelson. His most recent project, Blues Experience, finds him joining forces with Fleetwood Mac co-founder Mick Fleetwood for an exhilarating take on blues classics, reimagined through ukulele and percussion.

A passionate collaborator and storyteller, Shimabukuro channels joy, innovation, and pure musical spirit in every note. His concerts are dazzling celebrations of connection—proof that even the smallest instrument can carry the biggest sound.

Old Town New Folk is underwritten by Nick and Lorie Howley, with additional support from Doug and Sherri Montgomery, John and Marilyn Rintamaki, Nell Smets, and Michael Blades and Kathy Kilroy. 

Jon Langford

Old Town New Folk

Concert series sponsored by Blue Heaven (click here to view the full lineup →)
Musician and artist Jon Langford stands before a brick wall decorated with his own artwork, holding an acoustic guitar mid-strum. His serious expression contrasts with the vivid, folk-inspired imagery behind him, capturing the creative fusion of punk energy and Americana roots that defines his work.

Tuesday, March 3, 7pm

Helmerich Theater

$100 front row, $50 general admission

Wednesday, March 4, 7pm

Hugh’s View

$125 front row, $70 general admission

Welsh-born and Chicago-based Jon Langford is a musical shapeshifter—punk pioneer, country crooner, painter, radio host, and storyteller. A founding member of the legendary punk band The Mekons, Langford helped redefine what folk and country could be when filtered through the raw edge of rock and rebellion. His later projects, including The Three Johns and The Pine Valley Cosmonauts, reflect his lifelong curiosity and collaborative spirit, bringing together musicians across genres and generations.

A true renaissance man, Langford is also a prolific visual artist whose striking portraits of country icons such as Hank Williams and Johnny Cash have become emblematic of his deep affection for American roots music. Whether on stage or on canvas, his work hums with humor, humanity, and a restless creative energy that’s distinctly his own.

Old Town New Folk is underwritten by Nick and Lorie Howley, with additional support from Doug and Sherri Montgomery, John and Marilyn Rintamaki, Nell Smets, and Michael Blades and Kathy Kilroy. 

Rachael Sage

Old Town New Folk

Concert series sponsored by Blue Heaven (click here to view the full lineup →)
Singer-songwriter Rachael Sage poses against a colorful, abstract backdrop. She wears bright, patterned clothing, turquoise earrings, and flowers in her hair, radiating creativity and joyful energy.

Tuesday, February 17, 7pm

Helmerich Theater

$100 front row, $50 general admission

Wednesday, February 18, 6pm

Hugh’s View

$125 front row, $70 general admission

A vibrant force in folk-pop, Rachael Sage has spent her career defying categories and expectations. Since founding her own label, MPress Records, the New York-based artist has released a steady stream of colorful, heartfelt albums that blend poetic lyricism with infectious melodies. She has toured alongside icons such as Rufus Wainwright, Ani DiFranco, Shawn Colvin, and Judy Collins, and her live shows are known for their humor, vulnerability, and bold theatrical flair.

A six-time Independent Music Award winner and John Lennon Songwriting Contest Grand Prize recipient, Sage is also a visual artist and former ballet dancer who once performed with the New York City Ballet. Beyond the stage, she is a “cancer thriver” and passionate advocate, using her music to raise awareness and funds for causes from women’s health to youth homelessness. With her signature blend of resilience and radiance, Sage transforms every performance into an inspiring celebration of art and survival.

Old Town New Folk is underwritten by Nick and Lorie Howley, with additional support from Doug and Sherri Montgomery, John and Marilyn Rintamaki, Nell Smets, and Michael Blades and Kathy Kilroy. 

John McCutcheon

Old Town New Folk

Concert series sponsored by Blue Heaven (click here to view the full lineup →)
Folk musician John McCutcheon smiles warmly while holding a banjo across his chest. He wears a striped shirt and dark vest, standing before a wooden backdrop that evokes the roots and warmth of traditional folk music.

Tuesday, February 3, 7pm

Helmerich Theater

$50 general admission

Wednesday, February 4, 6pm

Moved to Helmerich Theater

$100 front row, $70 general admission

For nearly five decades, John McCutcheon has been a cornerstone of American folk music, earning the title of “folk music’s Rustic Renaissance Man” (Washington Post). A gifted multi-instrumentalist—master of guitar, fiddle, banjo, and especially the rare hammer dulcimer—McCutcheon is also a prolific songwriter, storyteller, and activist with more than 30 recordings and seven Grammy nominations to his name.

McCutcheon’s music is deeply rooted in tradition, shaped by his early apprenticeships with Appalachian masters in Kentucky coal camps, union halls, and country churches. From those beginnings, he developed a voice that bridges generations, blending traditional ballads, original songs, and rich storytelling. His artistry has earned praise from peers and icons alike: Pete Seeger called him “one of the best musicians in the USA,” while Johnny Cash hailed him as “the most impressive instrumentalist I’ve ever heard.”

Equally at home on festival stages, symphony halls, and school auditoriums, McCutcheon has built a career on connection—bringing audiences of all ages into the shared joy of music. His live performances are renowned for their warmth, humor, and vitality, leaving listeners with the sense they’ve spent an evening with an old friend.

Old Town New Folk is underwritten by Nick and Lorie Howley, with additional support from Doug and Sherri Montgomery, John and Marilyn Rintamaki, Nell Smets, and Michael Blades and Kathy Kilroy. 

Susan Werner

Old Town New Folk

Concert series sponsored by Blue Heaven (click here to view the full lineup →)
Musician Susan Werner performs on stage, smiling as she sings into a microphone while playing a grand piano under warm stage lights.

Tuesday, January 20, 7pm

Helmerich Theater

$85 front row, $50

Wednesday, January 21, 6pm

Hugh’s View

$100 front row, $70

Over the course of her twenty five year career, Susan Werner has earned a reputation as “one of the most innovative songwriters working today” (Chicago Tribune). With formidable chops on guitar (she began playing at age 5) and piano (she was a guest on Marian McPartland’s Piano Jazz), along with a graduate degree in voice performance, her shows are a one-woman master class in musicianship. Although best known as an acoustic songwriter that came up through coffeehouses and folk festivals, the Chicago-based artist has written songs in the style of Gershwin and Cole Porter (I Can’t Be New, 2004), gospel music (The Gospel Truth, 2007), traditional Cuban “son” (An American In Havana, 2016), and New Orleans junk piano (NOLA, 2019). In 2014 she composed the music and lyrics to the musical theater score Bull Durham, The Musical (MGM). Her songs have been recorded by Tom Jones, Michael Feinstein, and Shemekia Copeland, and her latest recording of originals, The Birds of Florida, took flight in 2022.

Old Town New Folk is underwritten by Nick and Lorie Howley, with additional support from Doug and Sherri Montgomery, John and Marilyn Rintamaki, Nell Smets, and Michael Blades and Kathy Kilroy. 

Southernmost Youth Orchestra Concert

Sunday, November 9, 5pm

Helmerich Theater

Free and open to the public

Experience the magic of the Southernmost Youth Orchestra! Join us for an inspiring performance by a talented group of young local string musicians. Under the direction of Irie Monte, these passionate performers bring energy, heart, and vibrant sound to every note. From classical favorites to contemporary selections, this concert showcases the rising stars of our southernmost community.

Swimming in the Dark
A Staged Concert of Act One

Cast & Crew Biographies

Martin Hennessy, Composer, is a prolific composer of opera and art song. With librettist Stephen Kitsakos, he composed An Incident in Sutton Square (finalist for the 2023 Dominic Argento Chamber Opera Prize), The Woman in Penthouse A, and The Pleasing Recollection: A Cabaret Opera. His opera A Letter to East 11th Street, with a libretto by Mark Campbell, was the first winner of the Domenic J. Pellicciotti Opera Composition Prize in 2014. Other chamber works include The Young King, with a libretto by Tom Rowan, commissioned by the University of Maryland; and The Good Friar, with a libretto by Mark Campbell, for the Center for Contemporary Opera and Urban Arias. His Ben Jonson Songs won grand prize at the San Francisco Song Festival, and he has been honored with Copland House and Millay Colony residencies as well as commissions from the Estate Project for Artists with AIDS and the Sorel Foundation. Recent commissions include Nous Deux, a setting of Paul Eluard’s incantatory love poem, for mezzo-soprano and string quintet, commissioned by mezzo-soprano Blythe Gaissert. He is currently commissioned by Madrid’s Teatro Real’s La Joven to write a new Maria Estuardo, with a libretto by Irma Correa.

Stephen Kitsakos, Libretto, is an opera librettist, theatre director and educator. Writing commissions include the National Endowment on the Arts, the American Opera Project, NYSCA, Catskill Watershed Corporation, ASCAP Foundation and The Woodstock Cycle for the Episcopal Diocese of NY. With Martin Hennessy he wrote the libretti for An Incident in Sutton Square (finalist for the 2023 Dominic Argento Chamber Opera Prize), The Woman in Penthouse A, and The Pleasing Recollection: A Cabaret Opera. With composer Sheila Silver he wrote the libretto for A Thousand Splendid Suns, commissioned by Seattle Opera, based on the bestselling book by Khaled Hosseini, nominated for “Best New Opera 2023” at the International Opera Awards in Warsaw, Poland. Other libretti for Silver include the chamber opera The Wooden Sword, and the Tibetan-themed operatic cantata The White Rooster, commissioned by the Smithsonian Institution. A member of the Theatre Arts Faculty at SUNY New Paltz for fifteen years, Kitsakos was a contributing writer at The Sondheim Review as well as Music in American Life for ABC-CLIO.

Michael Shell, Stage Director, is an Associate Professor of Music in Voice at the Indiana University Jacobs School of Music and Resident Stage director for the Jacobs School of Music Opera and Ballet Theater. His “visionary” and “masterful storytelling” (Opera News) is steadily leading him to be one of the most sought after directors in the United States. His “thoughtful and detailed score study” (Opera Today) is shown in character development and relationships onstage as well as the complete visual world he creates. Shell has directed productions for Atlanta Opera, Pittsburgh Opera, Michigan Opera Theater, Opera Omaha, Opera San Jose, Opera Tampa, Opera North, Virginia Opera, Santa Fe Opera, Wexford Festival Opera, and Opera Theatre of Saint Louis. He holds a B.M. and M.M. in Music/Vocal Performance from the University of North Carolina School of the Arts and was a Corbett Scholar at The University of Cincinnati College-Conservatory of Music.

Tyler Readinger, Conductor has served as cover conductor for the New York Philharmonic and Allentown Symphony Orchestra, assistant conductor of the Reading Philharmonic Orchestra, and guest conductor for the Reading Pops Orchestra. As a student of Arthur Fagen and Thomas Wilkins, he was assistant conductor for the Indiana University Opera and Ballet Theater. Tyler was named semifinalist in the 2022 V Nino Rota International Conducting Competition. He has participated in numerous other conducting programs, most recently being the VIII Atlantic Coast Conducting Competition and Masterclass. He is also an avid conductor of film music both in live-to-picture performances and recording sessions.

Rosi Ware, Narrator, is an inspirational speaker and ambassador of Arts & Culture in Key West. Formerly the CEO of Millward Brown, the world’s largest advertising research agency, and a consultant for Kantar & WPP, the world’s largest marketing services group, she was honored by Queen Elizabeth II in 1997 as one of 75 women in business who had made a difference to the UK. A Founding Board Member, and past President/Board Chair of The Studios of Key West, she was awarded “Humanitarian of the Year” in 2016 by the Red Cross for her work with disabled adults at MARC House. A Board Member and Past President of the Key West Garden Club, and Board Member of Art In Public Places, her hobbies include gardening, theater, literature, music, movies and travel. Rosi narrated the first NEA-funded workshop of A Thousand Splendid Suns which saw its world premiere at Seattle Opera in 2023.

Tomasz-Jedrowski

Tomasz Jedrowski, author, is a graduate of Cambridge University and Université de Paris. Swimming in the Dark is his debut novel and was the subject of a hotly contested six-way publishing auction. Bloomsbury gained the rights. It was one of the most popular LGBTQ books of 2020, and was selected as a Book of the Year by The Guardian, NPR, Attitude Magazine, O Magazine and others. It has now been translated into 18 languages. Tomasz was born in Germany to Polish parents. He speaks English, French, German & Polish. He is currently writing his second novel.

photo by Kuba Dabrowski

Deanne Meek

Mezzo-soprano, Deanne Meek* has had an active international career since the mid-1990’s appearing in major opera houses including La Scala, the Metropolitan Opera, Teatro Real (Madrid), Théâtre Royal de la Monnaie, Opéra de Lyon, Teatro Colón, Théâtre du Châtelet, Gran Teatre del Liceu & the English National Opera. In the US she has sung roles at the LA Opera, Dallas Opera, Washington Opera, Seattle Opera among others. She made her European debut as Donna Elvira in Mozart’s Don Giovanni in Dublin, followed by performances throughout the UK in roles such as Rosina in The Barber of Seville, Meg Page in Falstaff, Ruggiero in Alcina, and the title role in La Cenerentola. She champions contemporary works, creating the role of Ma Joad in Ricky Ian Gordon’s The Grapes of Wrath with Minnesota Opera and performing roles such as Jo March in Little Women & Mrs. DeRocher in Dead Man Walking. Meek appeared at The Studios of Key West as Fariba in the first opera workshop of A Thousand Splendid Suns in 2016.

michael-kelly-cropped

Praised as “expressive, dynamic & vocally splendid,” baritone Michael Kelly* is sought-after for his riveting interpretations of recital, concert and operatic repertoire. Mr. Kelly has recently performed at Santa Fe Opera, Carnegie Hall, with New York City Opera, the New World Symphony, Seattle Symphony and the Cincinnati May Festival. He performed Bernstein’s Mass with the Mostly Mozart Festival, and gave the World Premiere of a new chamber work by David Del Treidici at NYC’s Symphony Space. In recent seasons he has been heard in Schubert’s Die Schöne Müllerin, as Hannah Before in Kaminsky’s As One, Figaro in The Barber of Seville, Papageno in Mozart’s Magic Flute, Brahms’ Ein Deutsches Requiem, and the title role in the NY premier of Carlyle Floyd’s newest opera Prince of Players. In May, 2025, he will originate the role of Harvey Milk in the World Premiere of Harvey Milk by composer Stewart Wallace and librettist Michael Korie at Opera Parallèle. Kelly is known to Key West audiences for his solo performance at The Studios of Key West in The Pleasing Recollection, a Cabaret Opera, by Hennessy and Kitsakos.

A Chorus of Work Collective Students, Church Choir, Anti-Soviet Marchers and Police sung by the cast.

Cast from IU Jacobs School of Music
Abigail McKay Cherry, David Drettwan, Jonathan Elmore, Theo Harrah, Miranda Nilan, Zachary Olmoz, Ashley Ruckman, Kathleen Simunek, Michael Varilla

Orchestra
Tyler Readinger, Conductor
Matthew Gemmill and Andrew Becker, Piano
Thomas Frost, Percussion

The composer’s orchestration has been reduced for this performance from 12 players: Flute (doubling piccolo), Oboe, Clarinet in B flat, Bassoon, Horn in F, Percussion, Piano, and String Quintet

*Courtesy of AGMA, the American Guild of Musical Artists

Riff on ROXFILM

Film Screenings presented with Roxbury International Film Fest

The Roxbury International Film Festival is the largest New England festival dedicated to celebrating films by, for and about people of color around the world. The Studios, in conjunction with the festival, presents two films, Come On In by Daniel Callahan and Paul Laurence Dunbar: Beyond the Mask by Frederick Lewis. Both screenings are followed by talkbacks with the directors.

sponsored by Boston Global Bridge Institute

Film Screening

COME ON IN

Daniel Callahan

Friday, February 7, 7pm

Helmerich Theater

$18, $13 mbrs.

Callahan’s directorial debut centers on a jaded artist who returns home after not making it in the big city, only to find a life empty of meaning and a soul-emptying job. But when he encounters a mysterious voice at work an uncanny journey ensues in which the lines between his reality and fantasy, past and present, dream and nightmare begin to blur.

Film Screening

Paul Laurence Dunbar: Beyond the Mask

Frederick Lewis

Saturday, February 8, 7pm

Helmerich Theater

$18, $13 mbrs.

Paul Laurence Dunbar: Beyond the Mask explores the life of the first nationally renowned African American writer, known for poems like “We Wear the Mask” and “Sympathy.” Highlighting his literary legacy and activism against Jim Crow laws, the film features Maya Angelou and examines Dunbar’s complex navigation of race and art during the turn of the century.

Q&A with the Directors

Daniel Callahan is a multimedia artist, filmmaker and designer. Merging a legion of disciplines including painting, digital photography, film, music, writing and performance, Daniel works to craft immersive experiences incorporating story, ritual, and the human form to explore aspects of resilience and mysticism. Read more →

Frederick Lewis, a writer, director, and professor at Ohio University’s School of Media Arts & Studies, creates award-winning documentaries featured on PBS and screened at venues like the National Gallery of Art. A Presidential Teacher Award recipient, he’s taught globally, including as a Fulbright Specialist in Hungary. Read more →

Films introduced by ROXFILM Board Member Andrea Lyman

Andrea Lyman is honored to be invited to represent ROXFILM Festival at The Studios of Key West “Riff on ROXFILM”. Andrea on the board of Roxbury International Film Festival (RoxFilm Festival). She is currently the New England Local President of SAG-AFTRA (Screen Actors Guild-American Federation Of Television and Radio Artists), a co-director of the Actors Forum of The Secret Society Of Black Creatives and on the Executive Board of the Greater Boston Labor Council. She plays the Leah, the mother, in Daniel Callahan’s award winning film COME ON IN which premiered at RoxFilm Festival. She has enjoyed appearing in several films over the years at RoxFilm Festival and is in a few films that have been submitted for consideration in the upcoming RoxFilmFestival in June 20-July 2, 2025. She can be seen in films currently touring the film festival circuit such as UGLY SWEATER which is scheduled for its first LA screening at the Pan-African Film Festival and the horror film, CROOKED FINGER and romcom PLUS 1’S (premiered at RoxFilm Festival). Andrea has played real life characters in the historical docudrama films HALF THE HISTORY: ELLEN GARRISON: AN ACTIVIST’S STORY playing Ellen Garrison (she also plays Ellen Garrison in a special film created for the upcoming 250th celebration of Concord, MA) and in NEGRO ELECTION DAY playing the Phyllis wife of the King. Andrea truly loves singing and performed in the Boston stage productions of MOMOLOGUES: THE MUSICAL. She performs her one woman musical show BROADWAY LADY. Andrea has performed in Radio City Music Hall’s CHRISTMAS SPECTACULAR, ION-TV’s A SNOW WHITE CHRISTMAS.

ROXFILM is a multiple award-winning festival in the heart of Boston, MA. The festival, now in its 27th year, showcases films that celebrate and elevate stories of people of color around the world. The festival is a celebration of creativity and a testament to the power of storytelling, offering a platform for filmmakers to showcase their extraordinary talents and bring us stories that educate, entertain, and move us into action. The festival provides a platform for both emerging and seasoned filmmakers and is a center of cinematic excellence bridging cultures, and uniting individuals from all walks of life using the universal language of film. ROXFILM’s focus continues to be sharing stories so often not covered in the mainstream and even alternative media spaces. Through screenings, conversations, workshops, and hangouts, ROXFILM reminds us that film has the power to inspire us and build connections that go beyond cultural barriers.

MICROPARTY

Live Show

Friday, February 14, 6pm

Helmerich Theater

$35 adult, $20 child

Saturday, February 15, 3pm

Helmerich Theater

$35 adult, $20 child

Sunday, February 16, 3pm

Helmerich Theater

$35 adult, $20 child

Electric Blue Yonder, in partnership with Bravo Children’s Theatre, and Irie Monte’s Southernmost Youth Orchestra present an interactive live experience celebrating creativity and a love of learning. This unique performance fuses acting, live music, puppetry, and dance as it invites young explorers and their families to embark on a whimsical journey through a universe of unlimited imagination.

sponsored by Key TV