• A Sherlock Carol at Westport Country Playhouse

    Westport Country Playhouse 25 Powers Court, Westport

    December 13 - 21, 2025 Two literary legends collide when a grown-up Tiny Tim calls on Sherlock Holmes to investigate the mysterious death of Ebenezer Scrooge. This wildly inventive holiday mashup of Dickens and Doyle blends mystery, heart, and humor in a witty and wondrous theatrical treat. A New York Times Critic’s Pick and international […]

    $35 – $65
  • 8th Annual 12×12 Holiday Exhibit at Westport County Playhouse

    Westport Country Playhouse 25 Powers Court, Westport

    Celebrate the season with the Artists Collective of Westport at their 8th Annual 12x12 Holiday Exhibit. The free reception will be on Tuesday, December 16 from 6 to 8pm with food, beverages and music by Rock and Roll Hall of Fame inductee Mark Naftalin, of the Paul Butterfield Blues Band. The exhibit will be open […]

    $45 – $65
  • Ana Gasteyer – Sugar & Booze Holiday Spectacular at Westport Country Playhouse

    Westport Country Playhouse 25 Powers Court, Westport

    Ana Gasteyer will be bringing her Sugar & Booze Holiday Spectacular to the Westport Country Playhouse – performing favorites from Sugar & Booze, her album of seasonal favorites and holiday originals which topped numerous “Best Holiday Album” lists. For more information

    $95 – $125
  • Broadway Scores at the Playhouse: Big Band Broadway at Westport Country Playhouse

    Westport Country Playhouse 25 Powers Court, Westport

    January 29 - February 1, 2026 Tony-Award winner Debbie Gravitte leads a thrilling experience, with Broadway’s greatest hits meeting the bold brass and swinging rhythm of the Big Band era. From classic showtunes to modern favorites, Big Band Broadway is a dazzling revue of beloved songs delivered with sassy style and powerhouse vocals. It’s pure […]

    $45 – $65
  • Agatha Christie’s The Murder of Roger Ackroyd at Westport Country Playhouse

    Westport Country Playhouse 25 Powers Court, Westport

    July 14-August 1, 2025 A murder. A mansion. A mysterious cast of suspects. And only one man  can uncover the truth: Hercule Poirot. Agatha Christie’s The Murder of Roger Ackroyd is more than just a mystery—it’s the gold standard of the genre, widely hailed as “the greatest whodunnit ever written.” In this new adaptation by Mark Shanahan, […]

    $45 – $65