Labor Day Weekend with Hagerty Driver’s Club

Last week, I spent Labor Day Weekend sitting behind the wheel of a 1957 Ford Fairlane 500 Skyliner. The car belonged to Greg Riley who set up a classic car road trip through scenic east Texas with support from Hagerty Insurance Driver’s Club. Many of the people who were on this trip were Hagerty customers who brought along their insured pride and joys to partake in a Saturday morning drive through the of Sam Houston National Forest. Taking it slow and stopping to see some truly unique places.



The meeting point was a Kroger’s parking lot in Montgomery, TX at 8:30am. The ’57 Fairlane 500 glided over the concrete parking lot on its radial white walls. Minutes later a 1965 Honda 600 roadster rolled up and parked next to the Ford creating a spectrum in the range of cars that showed up for this Hagerty Driver’s Club meet. Jaguar E-type, Dodge Ram Adventurer, 911 Carrera, Subaru RS, patina Corvair, C3 Stingrays, Factory Five Cobra, and even a 1927 Cadillac sedan with a little field mouse riding shotgun.


From there we embarked on the scenic drive to Richards, TX, on a locally known road through the woods of the Sam Houston National Forrest. Our convoy of oil drippers turning heads from trucks towing boats, motorcycle crews on the side of the road, and adrenaline seekers riding 10-speeds.

Driving a 1957 Ford Fairlane 500 in 2019

What was it like to drive a car from 1957 with 1957 brakes? I felt like Captain Ishmael with no feel at the wheel on a two lane blacktop sea and Chuck Berry singing Beethoven. You don’t steer a luxury convertible from the 1950’s, you aim it into a turn and feel its weight transfer like a boat.

Sudden movements at the wheel could make the Fairlane do its best impression of Chubby Checker’s Twist. The FoMoCo V8 had bottomless low-end torque on tap, but too much foam in the glass to actually break the speed limit. Not that I wanted to go fast. The Fairlane’s drum brakes had me doing impressions of ABS with both feet… I loved driving that car. I felt like the king of the cowboys out shining everything on the road.

Last but not least, the Fairlane 500 Skyliner metal folding roof puts on a show as it emerges from its Corolla sized trunk lid and snaps on to the windshield like a giant red Lego piece.


Richards, TX

First stop was the little town of Richard, TX. Our convoy stopped at Richard’s Community Center located next to a row of antique buildings. The cars brought a nostalgic second wind to the buildings and created some great photo opportunities as the sun was still rising. Temperatures hadn’t reached their peak yet, and the astrosphere was happy as everyone walked around admiring the little town and each others cars.


Fanthrop Inn, Anderson, TX

While in Anderson the group stopped at the Fanthrop Inn State Historic Site to take in a free tour of a real stagecoach boarding house. Next to the antique house was a traditional unpainted wooden barn with a perfectly restored authentic stage coach. The Fanthrop Inn does offer occasional rides in the stage coach and I recommend checking out their website or social media to find out when the next ride will be.


The Grandview Manor at Thomas Ranch

The final stop was at a truly one of kind place at Bill Thomas’ Thomas Ranch. We first stopped at the front of the 3,000 acre properly to check out his restoration shop. I’ve never been inside a shop that had everything needed to fully build a car. Paint booth, sandblasting booth, lifts, upholstery equipment, and all the tools you’ll ever need. In terms of be a car collector Bill could be referred to as the Jay Leno of Texas.

The warehouse across from it had all of Bill’s “tomorrow” projects. All the cars waiting in line to be restored, and what a waiting list it is! A herd of Great Depression era Buicks, big finned Impala’s, cherry C2 Corvette, a Dodge Brothers sedan, and even an antique fire engine. In the center of the room sat a mean green 1970 Cadillac De Ville that Bill’s parents brought new and he still owns a 1973 Oldsmobile Tornado that he bought new from the showroom in his collection of desired metal.


The final stop was parking behind Bill’s Grandview Manor that sits on top of a big hill overlooking the property. A pair of Al Capone era Cadillac’s greets us with freshly polished chrome and spotless paint. A barn full of Barbeque is served for lunch as the group continues their conversations of remembering dates and reciting engine numbers. Parked all around us were some Bill’s restored collector cars keeping us company while we ate.


After dessert we were invited inside for a private concert in the concert hall of the Grandview Manor.The center piece is a century old church organ that demands attention with golden pipes that tower towards the ceiling. Music closes the mouths while opening the minds as the crowd sits in amazement watching this antique work of engineering artistry perform its purpose. The house itself is a true architectural work of art with details on top of details, and a story behind every piece of furniture.


Hanging with Hagerty

I want to give Hagerty a huge thank you for co-hosting the event with Greg and giving us a truly memorable Saturday drive. I would also like to thank Greg for trusting me to drive his 1957 Ford Fairlane 500, alone, on this trip. I don’t know too many people who would trust a millennial with a 62 year old car on drum brakes.

Listen to Greg’s podcast Garage Dlx airing on the Live365 App (free) every Saturday with me, and fellow auto-journalist Natan Tazelaar, co-hosting. Every week us three sit down to  talk about everything… so long as its car related, while playing the best driving music from all eras. Check it out!

Hagerty Driver’s Club hosts so many wonderful events year round, so checkout their website to find the event nearest you. Life is too short to not drive your classic car.

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