A HISTORIC
THEATER WITH
POWERFUL,
ONE-OF-A-KIND
EXPERIENCES.
A Sherlock Carol
The Playhouse holiday tradition returns by popular demand for its third consecutive year!
December 13 - 21, 2025
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Ana Gasteyer – Sugar & Booze Holiday Spectacular
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.
Monday, December 22 at 7PM
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Encore Club
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