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The Wilkinson Young Singers Fund is pleased to announce the winners of its inaugural competition. The judges were impressed by the high caliber of the singers who applied and extend their gratitude to all applicants for their commitment to enriching the Boston-area vocal music scene and for their interest in sustaining the legacy of baritone Donald Wilkinson.

First-prize winner:

Kaileigh Riess



Massachusetts native Kaileigh Riess received a Performance Diploma in Opera in 2021 from Boston University's Opera Institute, a highly selective two-year training program for emerging operatic artists. While at the Institute, she starred as Maria Bertram in Mansfield Park and as Anne Trulove in The Rake's Progress. She was named the third-place winner in the 2021 Jensen Foundation Vocal Competition and a Boston District winner in the 2021 Metropolitan Opera National Council Auditions, and she went on to compete in the finals of the 2021 Lotte Lenya Competition. Kaileigh received a Master of Music degree from the University of Southern California’s Thornton School of Music. During the summer of 2021, she sang with The Music Academy of the West as a vocal fellow. Learn more at

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Second-prize winner:

David Thomas Mather



Baritone David Thomas Mather is a versatile and adaptive vocalist, an avid early music practitioner, and a musical theater enthusiast. He thrives when performing in a variety of styles, most notably vocal chamber music, Lieder, and art song. A professional chorister, he sings primarily as a member of the Boston-based Carduus ensemble and works as a section leader and cantor. He recently debuted with The Boston Camerata in their production of Dido and Aeneas: An Opera for Distanced Lovers and their Play of Daniel project tour, and has appeared with the Boston Youth Symphony Orchestras, Lowell House Opera, the Utah Symphony Chorus, and the Grand Teton Music Festival Chorus. In May of 2021, he received his Master of Music degree in Historical Performance from the Longy School of Music of Bard College. Learn more at


Winterreise, D. 911, No. XXIV:

“Der Leiermann” by Franz Schubert

“Falling Slowly” from Once: The Musical 

by Glen Hansard and Markéta Irglová