Halloween Movies, Theater, and Entertainment Near Westport 2026

8 Halloween movies, theater, and entertainment near Westport

Movies, Theater, and Entertainment this weekend Oct 16–18

thru31Oct The Spirits of Sleepy Hollow CountrySleepy Hollow Illustration of a small witch and a friendly ghost performing on a red curtained stage as a costumed audience watches (The Spirits of Sleepy Hollow Country) thru1Nov Haunted Trolley: In Search of SasquatchEast Haven Illustration of a small character with arms raised on a stage with red curtains, glowing lanterns and a pumpkin audience (Haunted Trolley: In Search of Sasquatch) thru31Oct Irving's 'Legend' at Washington Irving's SunnysideIrvington Illustration of a small witch and a ghost performing on a theatre stage with a pumpkin, red curtains and a seated audience (Irving's 'Legend' at Washington Irving's Sunnyside) thru31Oct An Audience with PoeSleepy Hollow Illustration of a small theatre stage with red curtains where a smiling ghost and a witch perform for a costumed audience (An Audience with Poe)

Other Halloween categories near Westport

Illustration of two small costumed children and a witch among pumpkins, hay bales and autumn trees on a sunny lawn WestportFamily-Friendly Fall Activities36 family events Illustration of a Halloween gathering at dusk with a smiling ghost, costumed figures, glowing jack-o'-lanterns and lights WestportHalloween Food, Drink, and Parties9 parties & tastings Illustration of a small cottage with glowing windows, ghosts, jack o'lanterns and black cats under a full moon at dusk WestportHaunted Experiences23 haunted attractions Illustration of friendly ghosts on small town rooftops with pumpkins and glowing windows as two witches fly past a full moon WestportUnique Halloween Events8 unique events

About Movies, Theater, and Entertainment near Westport

For those seeking Halloween entertainment in and around Westport, a contrast awaits. Families might lean towards the theatrical haunts at Westport Country Playhouse, while film buffs can find outdoor screenings in New Haven. These distinct experiences offer different ways to embrace the season's darker side, from intimate performances to open-air movie nights.

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