Trail Drive-In

11075 Tamiami Trail North,
Naples, FL 34108

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Trail Drive-In

The Trail Drive-In opened on August 31, 1954, with the 1953 drama “The Hitchhiker" starring Edmond O'Brien and Frank Lovejoy. The second feature was the 1953 drama/comedy “An Affair with a Stranger” with Jean Simmons and Victor Mature. It was opened by Peter Flontek, dba as Trail Drive-In Theatre Inc. Eventually D. A. Haynes would be the owner until its closing.

It had a capacity of 300 cars. In the early-1970’s a flea market was held at the drive-in. In 1977, Robert Lust and Ferris Horn leased the drive-in on Saturdays and Sundays during the day for a flea market. It was called the Naples Flea Market. I believe the Trail Drive-In closed in late-1985. The drive-in theatre was demolished and the property is now retail shopping.

Contributed by Randy Studer

Recent comments (view all 2 comments)

ScreenTower on October 25, 2014 at 8:57 pm

I moved to Naples in 1972 and saw movies at this theatre such as “Jaws” and the “Gambler” at the twin in East Naples, among others. Also attended the flea markets at both. I moved away in 2004 and am sorry to see both are gone, but the memories will always be there. Please support the Drive-in’s that are still up and running!

MichaelKilgore on April 8, 2021 at 12:33 pm

Boxoffice, Oct. 12, 1959: “Murray & Fink Theatres … has purchased the Trail Drive-In at Naples, the purchase including all real estate at the site, with ample room for expansion of the airer. The circuit plans to build a trailer park on part of the site. Erich Gompertz will own one-third interest in the Trail Drive-In.”

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