These Drive-in Movie Theaters Near Westchester Are Family-Approved

Take in old-school entertainment at these Hudson Valley drive-in movie theaters within a one-hour drive of Westchester County.

Ever since the Hollowbrook Drive-In in Cortlandt closed in 1984 (it’s a golf course and residential community these days), Westchester residents have had to trek up through the lower Hudson Valley for an in-car, outdoor movie experience. While many considered it a throwback novelty, drive-ins experienced a surprise boom when COVID-19 shuttered movie theaters and restaurants across the country.

Now the drive-in scene is back like it never left and, while in the summer season, these Hudson Valley drive-ins are once again opening their doors (and gates) to fans of cinema and the great outdoors.

Fair Oaks Drive-In Theater

365 Bloomingburg Rd, Middletown, 845.316.2266

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Fair Oaks Drive-In is the definition of a classic drive-in theater right in the heart of Middletown. Tickets run either $30 per carload or $49 for a family pack that includes a 17oz popcorn, four bottled beverages, and one box of candy. Vehicles exceeding 10 passengers will not be permitted for certain events. Visit the drive-in’s Facebook page for movie screenings and updates.

Four Brothers Drive-In

4957 NY-22, Amenia, 845.373.8178

Owned by the folks who run the popular Four Brothers restaurant chain, Four Brothers is a one-stop shop for movie nostalgia. The theater is open seven nights a week, rain or shine, and runs double features that lean in the family, comedy, and drama directions. Uniquely, Four Brothers has its own EV charging stations, along with a delightful menu of concession food available for online and in-person ordering. Pets are welcome and can take advantage of the large onsite litter box. As for additional entertainment, the venue boasts a pergola, family swing, mini golf course, airstream, and food truck.

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Overlook Drive-In

126 Degarmo Rd, Poughkeepsie, 845.452.3445

Established in 1955, Overlook has a screen that’s as tall as a six-story building. As many as 750 cars can park to catch the nightly double feature — especially during peak season.

Warwick Drive-In

5 Warwick Tpke, Warwick, 845.986.4440

Established in 1950, the Warwick Drive-In continues to show top flicks to movie-loving Hudson Valley patrons in rain or shine. This plein-air theater runs up to six flicks on three screens, seven nights a week. What’s more, hungry patrons can order fresh, hot food, like popcorn chicken and nachos, along with the usual snack repertoire.


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