Greg DeCosta and Harvey Take Route 66 in a Classic Dream Car — the Black 1966 Cadillac Sedan DeVille

Last updated on 16 Sep 2026

Some memories don’t show up all at once—they arrive like highway signs at dusk, one after another, until you realize you’ve been traveling for miles inside them. For Greg DeCosta and Harvey, that kind of remembering has a shape: a long American road and a classic dream car that makes the world outside the windshield feel both brand-new and already gone.

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The 1966 Cadillac Sedan DeVille is a legendary representation of mid-century American automotive luxury, marked by its expansive presence, clean body lines, and commanding performance. Despite overall weaker auto sales in the United States in 1966, Cadillac achieved record success, producing 60,550 units of its pillarless four-door hardtop Sedan DeVille.

A pristine black-on-black variant represents one of the most classic, sought-after factory specifications for this model.

Key Specifications & Mechanics

The 1966 model year sat firmly in Cadillac's golden era of massive overhead-valve V8 engines, featuring standard luxury amenities that were highly advanced for the time.

The Powertrain: Driven by a 7.0-liter 429 cubic-inch V8 engine equipped with a 4-barrel Carter AFB carburetor. It featured a 10.5:1 compression ratio and hydraulic valve lifters, churning out an impressive 340 horsepower.
Transmission: Mated to a smooth 3-speed automatic transmission.
Standard Conveniences: Outfitted from the factory with power steering, power brakes, a power-adjustable driver’s seat, and power windows.

Exterior & Interior Styling

The triple-black aesthetic highlighted the sheer scale and crisp, architectural geometry of the 1966 redesign.

Feature	Standard "Black-on-Black" Configuration
Body Style	Pillarless 4-door hardtop sedan.
Exterior Highlights	Deep black paint complemented by a black vinyl roof, heavy brightwork chrome bumpers, and period-correct wide whitewall tires.
Upholstery	Factory choices included solid black leather upholstery or a premium black-and-gray leather and cloth split.
Dashboard & Trim	Crack-resistant black dashboard featuring a wide horizontal speedometer, chrome three-spoke steering wheel horn ring, and a folding center armrest.
Optional Tech	Premium variants featured advanced options like Automatic Climate Control air conditioning and the "Guide-Matic" Twilight Sentinel sensor, which automatically dimmed high beams for oncoming traffic.

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Greg DeCosta and Harvey Take Road Trip Down Route 66 In His Classic Dream Car A 1970 Chevy Red Corvette Stingray

Known as The Mother Road, spans roughly 2,448 miles (3,940 km) through eight states, beginning in Chicago, Illinois, and ending at the Santa Monica Pier, California.

While the road was officially decommissioned in 1985, about 85% of it remains drivable today via historic alignments and state highways.

Ultimate Route 66 Adventure: Must-See Stops!

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Essential Planning Tips

Duration: A minimum of 14 days is recommended to see the major highlights without rushing. A leisurely pace can take up to 3 weeks.

Timing: Spring (May) and Fall (September to October) offer the best weather and fewer crowds. Summers are extremely hot in desert stretches, and winters can bring road closures in the north.

Navigation: Traditional GPS often defaults to interstates. Use specialized resources like the Route 66 Navigation App or the EZ66 Guide for Travelers to stay on the historic path.

Centennial Celebration: The year 2026 marks the Route 66 Centennial, featuring special events and tours across all eight states.

Top Must-See Stops by State

Illinois: The "Begin Route 66" sign in Chicago

and the Cozy Dog Drive In (birthplace of the corn dog) in Springfield.

Missouri: The Gateway Arch in St. Louis

and the Meramec Caverns, which feature vintage barn advertisements.

Kansas: The shortest stretch (13 miles), featuring Cars on the Route in Galena.

Oklahoma: The Blue Whale of Catoosa

and the futuristic Pops 66 soda ranch in Arcadia.

Texas: The Cadillac Ranch in Amarillo

and the Midpoint Café in Adrian, the mathematical center of the route.

New Mexico: The historic Blue Swallow Motel in Tucumcari

and the Spanish-influenced plaza in Santa Fe.

Arizona: The Wigwam Motel in Holbrook, Standin' on the Corner Park in Winslow, and the gateway to the Grand Canyon in Williams.

California: The desolate Roy's Motel & Café in Amboy

and the iconic End of the Trail sign at the Santa Monica Pier.

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