A gala evening celebrating 95 Years of the Westport Country Playhouse!

Don your festive attire and enjoy an unforgettable evening of entertainment, delicious food and cocktails by Diane Browne Catering, raffle prizes, auction items, Pre-Show Reception, plus a Post-Show Party — all in generous support of the Playhouse.

Stay tuned for updates as we announce our 2026 Artistic Honoree, who will be celebrated alongside our 2026 Leadership Award Honoree, Joyce Hergenhan.

Attire: Semi-Formal
Attire: Semi-Formal: Please join us in semi-formal attire. While the evening is special, formal gowns and tuxedos are not required. Semi-formal is just right!

Schedule of Events

5:30PM
Pre-show reception: Cocktails, hors d’oeuvres, live music*

7PM
Performance: Live Auction, Presentation of Awards to Nathan Lane and Anne Keefe, and Performances by guests to be announced soon

9PM
Post-Show Reception in the Sheffer Studio

*Sponsor packages, $750 tickets and $500 tickets include pre-show cocktail party, ticket to the performance, and post-show reception. $250 show tickets include ticket to the performance and post-show reception only.

View Images from last year's gala honoring nathan lane and anne keefe!

Anne Keefe, Leadership Award winner, and Nathan Lane, Artistic Honoree. Photo by Kerry Long Photography

Pre-show reception. Photo by Kerry Long Photography

Pre-show party music by Westport's Chris Coogan. Photo by Kerry Long Photography

Ray Roderick, Brad Aspel, and Cory English. Photo by Kerry Long Photography

Nikki Renée Daniels. Photo by Kerry Long Photography

Scarlett Strallen. Photo by Kerry Long Photography

Stephanie Pope. Photo by Kerry Long Photography

Christine Pedi. Photo by Kerry Long Photography

Marissa Rosen. Photo by Kerry Long Photography

Michael Wordly. Photo by Kerry Long Photography

Melinda Dolittle. Photo by Kerry Long Photography

Danny Burstein. Photo by Kerry Long Photography

Santino Fontana. Photo by Kerry Long Photography

Cady Huffman. Photo by Kerry Long Photography

Krysta Rodriguez. Photo by Kerry Long Photography

Curtain call. Photo by Kerry Long Photography

TICKET SPONSORSHIPS

Platinum Sponsor

$15,000

8 premium seating tickets, prime reserved table for pre-show reception, champagne bucket, year-long parking pass, & sponsor listing

Gold Sponsor

$10,000

6 premium seating tickets, reserved table for pre-show reception, champagne bucket, year-long parking pass, & sponsor listing.

Silver Sponsor - SOLD OUT!!

$5,000

4 premium seating tickets, reserved table for pre-show reception, champagne bucket, year-long parking pass, & sponsor listing.

Sponsorship tickets are available by contacting Rick Davis at (203) 571-1131 or rdavis@westportplayhouse.org

INDIVIDUAL TICKET OPTIONS

$750 TICKET

Premium theatre seat PLUS Pre- and Post-Show receptions!

$500 TICKET

Standard theatre seat PLUS Pre- and Post-Show receptions!

$250 Show TICKET

Standard theatre seat PLUS Post-Show reception! This ticket does not include the pre-show party.

Gala and Fundraisers

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.

Learn about upcoming and past galas and fundraisers HERE!

THANK YOU

2026 Programming & Season Sponsorship is generously provided by Barbara Streicker.

Media Sponsorship for the 2026 season is generously provided by Moffly Media and WSHU Public Radio.

All titles, dates, and artists are subject to change.

Saturday, October 3, 2026

Gala 2026

Come revel in 95 years of the Playhouse!

Get tickets

$750 and $500 include pre-show reception, performance, and post-show receptioin

$250 show tickets include performance and post-show reception only.