Halloween Movies, Theater, and Entertainment Near Middletown 2026

7 Halloween movies, theater, and entertainment near Middletown

Movies, Theater, and Entertainment this weekend Oct 23–25

Fri23Oct Candlelight: A Haunted Evening of Halloween ClassicsMount Kisco Illustration of a skeleton drummer, a witch guitarist and a pumpkin headed band playing on an outdoor stage at night (Candlelight: A Haunted Evening of Halloween Classics) 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) 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 Middletown

Illustration of costumed clay children and a witch playing among pumpkins, hay bales and tents on an autumn lawn MiddletownFamily-Friendly Fall Activities37 family events Illustration of a Halloween party at dusk with costumed characters around a punch bowl, a ghost, pumpkins and string lights MiddletownHalloween Food, Drink, and Parties3 parties & tastings Illustration of a small haunted cottage with glowing windows, ghosts, jack-o'-lanterns and a black cat under a pale moon MiddletownHaunted Experiences19 haunted attractions Illustration of a Halloween town at dusk with glowing houses, pumpkins, floating ghosts and a witch flying past a full moon MiddletownUnique Halloween Events14 unique events

About Movies, Theater, and Entertainment near Middletown

As Halloween approaches, Middletown residents can find seasonal entertainment with outdoor movie nights and indoor theatrical performances. Consider the Raleigh drive-in movie for a classic double feature, or experience a unique theatrical interpretation of Poe in New York City.

For those seeking a different kind of literary immersion, Irving's 'Legend' also beckons from New York City. And in White Plains, the Candlelight series offers a haunting musical program.

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