Every year, we offer a series of fundraisers to benefit various programs at the Playhouse. All proceeds go directly to support our non-profit, professional, producing theater and its work on stage, with schools, and throughout the community.
2025 FUNDRAISERS
At This Stage
Saturday, October 4, 2025The Fitzgeralds
Saturday, September 27 at 7pmPasek & Paul: Waving Through Westport
Monday, June 23, 20252nd Annual Golf Tournament at Birchwood Country Club
Monday, July 21, 2025LOAD
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2024 FUNDRAISERS
An Evening with Audra McDonald
Saturday, February 10, 2024An Evening with Bernadette Peters
Sunday, May 19, 2024The Best Is Yet To Come
Saturday, September 14, 2024A jazzy and joyful evening honoring Kristin Chenoweth and Mary-Mitchell Campbell! The 2024 Leadership Award will be presented to Westport’s own Harold Bailey, Jr. and Bernicestine McLeod Bailey.
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2023 FUNDRAISERS
An Evening with Justin Paul & Friends with Kelli O’Hara & James Naughton
Saturday, September 9, 2023Patti LuPone: Don’t Monkey with Broadway
Saturday, June 15, 2023PAST BENEFITS
Multi-award-winning Broadway star Renée Elise Goldsberry performs at the 2022 Gala, Back to the Playhouse!, with Jordan Peters, guitar/music director. Photo Credit: Coppola Photography.
Oscar, Grammy, Tony, and Olivier Award-winning creator Justin Paul (Dear Evan Hansen, La La Land, The Greatest Showman) addresses the audience at the 2023 Gala, An Evening with Justin Paul and Friends with Kelli O’Hara and James Naughton. Justin Paul graduated from Westport’s Staples High School in 2003, and was a member of Staples Players. Photo Credit: Jerri Graham Photography.
The 2019 Gala features Sirius/XM®️ radio personality Seth Rudetsky and Tony Award-winning Broadway star Kelli O’Hara headlining Black & White Ball: A De-Lovely Evening, Photo Credit: samuelstuart.com
Two time Tony Nominee Jonathan Groff performing at our 2017 Gala. Photo credit: Steve Walter
Our 2006 Gala, The Ladies Who Sing Sondheim, featuring (L-R): Kristin Chenoweth, Laura Benanti, Stephen Sondheim. Photo by Kathleen O'Rourke
Playing Our Songs, the 2011 Gala, including (L-R): Karen Ziemba, Max van Essen, Bernadette Peters (honoree), James Naughton, Eliabeth Stanley, Andrew Rannells. Photo by Kathleen O'Rourke
(L-R): Tony Bennett, Audra McDonald, James Naughton, Paul Newman, Glenn Close, Joshua Bell in 2005 Celebrating Joanne Woodward. Photo by Kathleen O'Rourke
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