2025 LINEUP
WABAN ALLEY PARK STAGE
TIME : 2:30PM
The Outskirts is a garage band playing mostly originals, hard & harmonious: Jessie Leaman guitar & vocals, Jodie Treloar Sampson accordion and vocals, Jim Orr bass, Chris Seidel drums.
The Outskirts
Dana Williams
Dana Williams blends soulful storytelling with jazzy elegance, crafting music that transforms vulnerability into beauty. Raised in Los Angeles by legendary guitarist David Williams (Michael Jackson, Madonna), Dana draws inspiration from jazz icons like Ella Fitzgerald and Billie Holiday, infusing her sound with timeless warmth.
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Her breakout single “Keep Me Waiting” was featured in Whiplash, and she’s since released fan favorites like “Fooling Myself” and “Honey,” amassing over 9 million streams.
WABAN ALLEY PARK STAGE
TIME : 3:30PM
Known for her genre-blending collaborations, Dana has worked with Freddie Gibbs, Boogie, Zach Hood, Alex Aiono and most notably Kaytranada, Rejjie Snow, and Aminé on the hit “Egyptian Luvr” (103M+ streams).
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Beyond her own releases, Dana’s music has appeared in campaigns (Aveda, Vanguard) and shows including Harlem, Love Island USA, and The Sex Lives of College Girls.
In 2025, Dana enters a new chapter with the release of her first full-length album, Real Friends. More than just a collection of songs, the album stands as a testament to resilience, vulnerability, and the power of creative community. It's a deeply personal project, shaped by the unwavering support of friends and collaborators who have championed her vision. Real Friends marks a significant milestone in her artistic journey—a celebration of growth, connection, and authenticity.
Nanauwe
WABAN ALLEY PARK STAGE
TIME : 4:30PM
Nanauwe, an Indigenous singer, songwriter, and producer from the Wôpanâak (People of the First Light) tribe, was born and raised in the woods of Noepe (Martha's Vineyard). Blending traditional Indigenous sounds with contemporary music, she creates immersive works rooted in ancestral wisdom and nature’s rhythms.
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A dedicated advocate for cultural preservation and environmental activism, she uses her platform to raise awareness on issues facing Indigenous communities and to protect ancestral knowledge and the planet. Through her music and advocacy, Nanauwe fosters healing, empowerment, and remembrance, ensuring her people’s voices endure for generations.
Dwight & Nicole
Genre defying DWIGHT + NICOLE can trace their musical roots through blues, R&B, and soul with a little roots rock, alternative, and Americana sprinkled in. DWIGHT + NICOLE have been Nominated for 10 Boston Music Awards, 10 New England Music Awards, and 11 Daisie awards, winning multiple "Band of the Year", "Vocalist of the Year", "Best Blues/R&B Band", "Female Vocalist of the Year", "Blues Act of the Year" and "Video of the Year”.
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Ritcher and Nelson met in Boston, Massachusetts fresh out of college. Cutting their teeth on the local club circuit, they each fronted popular area bands, and discovered a shared obsession of soul & blues greats like the Staples Singers, Albert King, and Etta James.
WABAN ALLEY PARK STAGE
TIME : 5:30PM
They began singing together and developed a close friendship that grew over time culminating in the formation of Dwight & Nicole. They started out as a duo with Dwight on electric guitar and Nicole on tambourine, stomping their feet for the beat and singing in harmony. After a move to Burlington VT, they met powerhouse drummer Ezra Oklan (Nicole Atkins, Elle King) and the group quickly formed a trio with Nelson picking up the bass. Now they also feature keyboard wizard Leon Campos.
With numerous releases under their belts, their most recent “The Jaguar, The Raven, and The Snake” just received the deluxe treatment in August of 2024, with the addition of the single, “Saying Goodbye.” Produced by acclaimed producer Joel Hamilton and recorded at his Studio G in Brooklyn and Ocean Sound in Giske, Norway throughout 2022. Album tracks feature the band with guests the Daptone Horns and Arkai Strings, amongst others.
esperanza spalding
Born in 1984 in Portland, Oregon, esperanza spalding is an eaabibacliitoti* artist,
trained and initiated in the North American (masculine) jazz lineage and tradition. Her
work interweaves through various combinations of instrumental music, bass playing,
improvisation, singing, composition, poetry, dance, therapeutic research, storytelling,
teaching, regenerative agriculture, urban land & artist-sanctuary custodianship, and
growing in love as a daughter, sister, cousin, niece, auntie, great-auntie, friend, while
collaboratively decolonizing within and through her hometown community. She founded
and Co-Directs Prismid Sanctuary, a non-profit that creates and stewards free artist
residency, performance, and workshop space in Portland, Oregon (Prismid.org).
WABAN ALLEY PARK STAGE
TIME : 6:30PM
Milton + esperanza is spalding’s first new album release since 2021's songwrights
apothecary lab, which along with 2019’s 12 Little Spells, both won GRAMMY Awards
(Best Jazz Vocal Album). Last year spalding released a protest song entitled “Não Ao
Marco Temporal” that was recorded in Rio and addresses the Temporal Framework, an
initiative in Brazil that threatens Indigenous Brazilians’ land rights and poses a major
risk to the Amazon rainforest. A 5-time GRAMMY winner and 11-time nominee,
spalding has previously released 8 full length albums and in addition to working with her
heroes including Nascimento and Shorter, she has collaborated with Q-Tip, Janelle
Monae, Robert Glasper, Terri Lyne Carrington and many others.
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esperanza continues to develop a mockumentary titled “NIGREDO” in collaboration with
brontë velez // to research, develop and share liberation grammars in jazz and black
dance // creative consults and collaborates for upcoming productions of the opera
“…(Iphigenia)” (music by Wayne Shorter, libretto by spalding) // and through the
Songwrights Apothecary Lab collaborates with practitioners in various fields relating to
sound, healing, and cognition to develop music with enhanced therapeutic potential.
With her dance project “Off Brand gOdds” and her therapeutic music incubator
“Songwrights Apothecary Lab” she co-leads performance, teaching, workshop, and
therapeutic-arts research residencies in collaboration with colleges and arts venues
across the Americas and throughout the world. She is a 2024 recipient of the Doris
Duke Foundation Artist Award and a 2016 Ford Foundation “Art of Change” Fellow.
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*European-African ancestored being influenced by American cultures living in
Indigenous Territories of Turtle Island
Rose Guerin
WABAN ALLEY PARK STAGE
TIME : 8:15PM
Rose Guerin is a Martha’s Vineyard musician, co-founder of LADYFEST, and The Supporting Local Music Project, dedicated to using the tools she has learned as a career musician to highlight community needs and raise money and awareness through her music.
She is a founding member of Vandaveer, touring extensively throughout the US and Europe. A staple at The Ritz the past few years, she has been entertaining folks with her original compositions and rockin’ covers with a myriad of stellar musicians worldwide for decades.
