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

Courtesy Four Brothers Drive-In

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

By Sabrina Sucato
Additional research by Carey Gallagher

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 recently experienced a surprise boom as COVID-19 shuttered movie theaters and restaurants across the country.

Now, with summer in full swing, we thought this would be a fine time to remind you of the fan-favorite local theaters you can hit that are only about an hour or less away from Westchester County.

Looking for something a little more local?
Click here for our guide to pop-up outdoor movies in Westchester.

Fair Oaks Drive-In Theater

Middletown, 845.316.2266

Fair Oaks Drive-In is the definition of a classic drive-in theater right in the heart of Middletown. Tickets run either $25 per carload or $45 for a family pack that includes a jumbo popcorn, four 16 oz sodas or water, 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

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 vehicle 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, a family swing, a mini golf course (not currently available for use), an airstream, and a food truck.

Photo courtesy of Four Brothers Drive-In

Hyde Park Drive-In

Hyde Park, 845.229.4738

With 12 acres and room for more than 600 cars at capacity, this Route 9 establishment has been a crowd-pleaser since 1950. Discount books are available to catch all the best steals. Along with pretzels and fried dough, the concession stand sells Black Angus burgers and cappuccinos. For updates on showtimes and COVID-19 protocol, visit the drive-in’s Facebook page.

Overlook Drive-In

Poughkeepsie, 845.452.3445

Established in 1955 — and run by the same family that owns the Hyde Park Drive-In — 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. For updates on showtimes and COVID-19 protocol, visit the drive-in’s Facebook page.

Warwick Drive-In

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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