Retro Road Trips: Motels Of The ’50s, ’60s And ’70s

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– Posted on August 29, 2025

Text by Patrick Bell.

The last holiday of summer is upon us, so let’s hit the road and get one last blast before winter sets in.  We have a variety of motels to see today, some that were the destination, and others that most likely were overnight stops along the way.  Plus the cars that people traveled in.  Climb aboard and we will get started.

Our first stop is the Captain’s Bounty on the Beach Motor Inn on Beach Street in Rockport, Massachusetts.  It currently looks much the same, with updated colors and a different Captain.  As the name suggests, it is actually on the beach, which is on the other side of this building.  From the left was a well worn ’65-’67 Volkswagen Type 1, a ’71 or ’72 Mercury Cougar XR-7 that had a Connecticut license plate, perhaps with a vanity or amateur radio operator number, a ’72 Chevrolet Townsman wagon with a license plate I can’t read, and maybe just the nose of a ’71 full size Oldsmobile.  The man looked like he may have been thinking, “Let’s get this show on the road”.

We are now at the Breeze Motel where they had showers and tubs, but I could not establish a location.  It appears like it was on a hill where it was likely breezy, and on the photo day it was overcast and cool as the gentleman was wearing a jacket.  He was standing by a V8 powered ’57 Nash Ambassador Super Country Club Hardtop, and to its right were two ’59 models; a Chevrolet Impala convertible and a Pontiac Catalina Sedan.

There is not much to go on for location in this one, other than what may have been swamp coolers on the roof.  It was a very typical design for a roadside motel in the fifties and sixties.  From the left a ’57 Cadillac Sixty-Two or Sixty-Two Sedan deVille with perhaps an Iowa license plate, a ’54 Buick Super 2 door Riviera possibly from Wisconsin, and a ’58 Plymouth Plaza Club Sedan with Sportone trim.

Now we are off to St. Petersburg, Florida, to the Skyway Motel and the neighboring Toll House Restaurant.  There is now an Olive Garden restaurant and a Tint World shop at that location.  Passing by was a ’57 Chrysler Windsor 4 door hardtop with possibly a ’59 issue Florida license plate.

Two more roadside type motels in a hilly and wooded area, but unknown location.  In the foreground was a ’57 Mercury Monterey 4 door sedan, and across the way at the Breeze Manor a ’61 Chevrolet full size wagon was parked in front of a room.

Let’s head west to the Normandy Inn on Ocean Avenue in Carmel-by-the-Sea, California.  Little has changed since this image was taken sixty-five or so years ago.  Two ’59 Cadillacs were parked out front; on the left was a Six Window Sedan of either the Sixty-Two or Sedan de Ville flavor, while the convertible was a Sixty-Two series.  The wagon was a ’59 Oldsmobile Super 88 Fiesta, and on the right a ’57 Plymouth Belvedere Sport Coupe Hardtop. Beyond the Plymouth was a Volkswagen Type 1.

Another unknown location with a typical middle priced motel style that appears to be in a community.  Parked out front starting in the foreground a ’60 Pontiac Catalina Sedan, ’56-’58 Hillman Minx Saloon, a ’54 Buick 4 door sedan that could have been any of the four trim series, ’60 Chevrolet Impala Sport Sedan, and on the end a ’58 Chevrolet Delray or Biscayne 4 door sedan.

A Travel Information Center of some sort with a Texaco station and a motel in the background.  In the foreground, a group of folks were leaving their ’60 Chevrolet Impala Sport Sedan and heading inside.

On the left edge, a ’59 Oldsmobile Dynamic 88 or Super 88, followed by a ’57 Ford Fairlane 500 Skyliner, a six cylinder equipped ’55 Chevrolet Two-Ten 2 door sedan, a ’62 Plymouth Savoy or Belvedere wagon, another ’57 Ford, a red ’58 Chevrolet Impala convertible, and the last one was a ’62 Impala.  It and the Plymouth wagon were the newest that I can see.

Here was a nice looking establishment, with some kind of stone fascia and flowers blooming in the flower beds.  It looked like an early fall day with the leaves beginning to turn, plus the lady was wearing a scarf and sweater.  She was posing beside a V8 powered ’67 Chevrolet Chevelle Malibu Sport Coupe with a same year Michigan license plate.  It was registered in Van Buren County, where the seat is Paw Paw (yes, you read that correctly).  On the left looks like a ’66 Buick Wildcat Custom Sport Coupe.

Our final stop is at the Pacific Sands Motel at a location I can’t verify.  California is a safe guess, and there was one in Santa Monica, but I could not find any images that would come close to resembling this one.  Parked underneath three females was a ’70 Buick Skylark 2 door sedan with an aerodynamic roof top carrier and cargo combination, and some quarter panel damage.  On the other side of it was a dark color ’71 Chevrolet Impala, and sticking its nose in the photo a white ’60 Ford Falcon.

Thanks for joining us and have a safe Labor Day holiday!

 

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