Westport Christmas Shows 2026

This holiday season, prepare for a captivating theatrical experience as 'A Sherlock Carol' returns to the Westport Country Playhouse. The beloved tradition blends the worlds of Charles Dickens and Sir Arthur Conan Doyle, following a grown-up Tiny Tim as he...

Embark on a magical holiday journey with Barnaby the elf and his reindeer companion as they race against time to save Christmas. This charming production, praised as an 'adorable holiday gem,' explores the true spirit of the season, celebrating Christmas,...

Gary Hoey's Ho Ho Hoey Rockin' Holiday Tour features guitarist Gary Hoey and his son Ian Hoey performing rock and blues, including solos, classic hits, and material from Hoey's album Avalanche.

Step back in time and experience the magic of Charles Dickens's 'A Christmas Carol' at the historic Old Dutch Church in Sleepy Hollow, NY. Master storyteller Jonathan Kruk, accompanied by musician Jim Keyes, delivers a captivating adaptation of the classic...

Derek Hough's 'Dance for the Holidays' features Hough and dancers performing holiday songs with choreography and stage production. The show includes classic carols and contemporary pop hits.

The Fairfield University Glee Club presents its annual Christmas concert, 'A Feast of Carols.' This year's program celebrates American Christmas music, featuring beloved tunes from historical hymns to modern classics. The concert includes a festive brass ensemble and invites the...

Step into a festive winter wonderland with Irving Berlin's White Christmas, a heartwarming musical at Curtain Call Inc. Follow two charming veterans on a romantic quest to a Vermont lodge, filled with song, dance, and holiday cheer. This uplifting production...

For 30 years, Rob Mathes has kicked off the holiday season with a spectacular concert. This high-energy event features Mathes, his all-star band, and a chorus, delivering a unique blend of rock, jazz, and blues with fresh takes on holiday...

Experience the magic of the season with 'Holiday in The Warehouse,' a heartwarming cabaret show featuring acclaimed singers Maureen Hamill, Mary Richard, and Kerry Lambert, accompanied by music director David Harris. They will present a delightful program of Broadway favorites,...

Experience the magic of the holidays with the Norwalk Symphony Orchestra's 'Holiday Pops' concert. This festive celebration features beloved seasonal classics, from Tchaikovsky's 'Nutcracker' to Handel's 'Messiah,' alongside popular tunes like 'Sleigh Ride.' The performance includes captivating choruses, dancers, exciting...

Step back to Christmas 1183 at Chinon Castle for a dramatic tale of the Plantagenet royal family. Witness King Henry II and Queen Eleanor of Aquitaine navigate treacherous succession plans for their three sons. This play promises a festive night...

Experience the magic of 'A Christmas Carol' as a vibrant musical at the John W. Engeman Theater. This production brings Ebenezer Scrooge's transformative journey to life, complete with visits from Marley and the ghosts of Christmas Past, Present, and Future....

Experience the magic of the season at the Eastview Winter Concert. This special event showcases the musical talents of Eastview students, offering a delightful evening of festive performances. It's a wonderful opportunity to enjoy holiday cheer and support young musicians.

Experience the magic of "Miracle on 34th Street" as a captivating musical at the historic Shubert Theatre. This heartwarming holiday classic, featuring a book and score by Meredith Willson, brings to life the story of Doris Walker and her encounter...

The Eglevsky Ballet presents a magical rendition of The Nutcracker, featuring a live orchestra conducted by David Bernard. This enchanting performance showcases the professional company and academy students in a holiday classic complete with a growing Christmas tree, a magical...