Curbside Musings: 1966 Lincoln Continental Convertible – Living Larger

1966 Lincoln Continental convertible. Edgewater, Chicago, Illinois. Sunday, September 28, 2025.

“Cooler By The Lake” read some of the banners in my Chicago northside neighborhood of Edgewater.  This could be a reference to how the breezes off nearby Lake Michigan keep things nice and cool in the summer, but it also refers to the beautiful multiculturality and artful, relaxed feel of this area.  It could just as accurately symbolize the car-spotter’s haven it is during warm weather months.  The sighting of this ’66 Continental convertible at the end of this past September was only one such example of many this year.

1966 Lincoln Continental convertible. Edgewater, Chicago, Illinois. Sunday, September 28, 2025.

The whole idea of a four-door convertible from a mainstream, luxury automaker exudes opulence.  Cadillac may have had the volume in the ’60s, but in my eyes and for style and with the exception of the brilliant ’67 Fleetwood Eldorado, the decade belonged to Lincoln.  I’ll admit that any classic car that’s decades old will automatically have built-in prestige and exclusivity by dint of its survivorship and relative rarity, but I’d argue that even without that (and it really is impossible to know), this Lincoln says “money” more and better than anything else currently on the new-car market.  No Navigator or Escalade can touch it.

1966 Lincoln Continental convertible. Edgewater, Chicago, Illinois. Sunday, September 28, 2025.

I also like the idea of a four-door convertible taking away the excuse of at least a few people who wouldn’t want to go for a ride because a convertible would be “too cramped” in the back.  Rear seat passengers get their own pair of doors, and there was also the three-inch wheelbase stretch for ’64, up to 126 inches from 123″, that had contributed significantly to rear legroom back there.  What good is all this luxury if the owner can’t share it, at least when he or she wants to?  I remember wanting to show off my new-to-me ’88 Mustang to friends and relatives and wanting to take them for a ride.  The rear seat wasn’t a complete torture chamber from what I can remember (when I had given someone else the keys to drive), but I could see how ingress and egress in my little Mustang hatchback might not have been the easiest things for my aunts and uncles who were, at the time, in the same middle-age bracket where I am now.

1966 Lincoln Continental convertible. Edgewater, Chicago, Illinois. Sunday, September 28, 2025.

I imagine that when new, a car like this Lincoln might have been owned by a fifty-something business owner and his wife, whose children were by then adults themselves and out of the house.  This would be the perfect car for a long drive after the extended family had gotten together for Sunday “dinner”.  (That’s lunch for most people; dinner is called “supper” in some parts of the Midwest, or at least it was in my family of origin.)  Everyone can fit, including a couple of grandchildren on laps.  Wind buffeting wasn’t an issue, because no one was in a hurry to go anywhere in particular.  The joy was in the journey.  The occupants of this beautiful Continental were traveling at a leisurely pace – seeing and being seen.  Look at my prosperity and gaze thee upon the beauty of my automobile.  Hey, if one could afford a rolling sculpture like this, would it be so wrong to want to bask in the glow in the admiration of others?  I’m sure that for some, that was and is the whole point.

1966 Lincoln Continental convertible brochure pages, as sourced from www.oldcarbrochures.org.

I had been aware of the greatness of these Continentals of the ’60s starting in my adolescence in the ’80s, but being able to easily identify their yearly changes had largely eluded me.  Even prior to sitting down to write this, it hadn’t even occurred to me that the ’66 had featured fully restyled sheetmetal.  It was a larger car than the ’65, not only in length, which had stretched about four and half inches (from 216.3″ to 220.9″), but also in width (from 78.6″ to 79.7″).  Height remained about the same as before at around 54.5″.

1966 Lincoln Continental convertible. Edgewater, Chicago, Illinois. Sunday, September 28, 2025.

Now that I’m aware of the ’66 being something of a generational bisector for this generation of Continental, it’s easier to notice at a glance the more sculpted sheetmetal that also included a full-length beltline character line just below the greenhouse that stretched from stem to stern.  Taillamps were also now set in the bumper, a dubious styling trend that I’m glad had had its place in time and then gone away, though their placement here doesn’t really detract from this car’s overall look of elegance.

1966 Lincoln Continental convertible. Edgewater, Chicago, Illinois. Sunday, September 28, 2025.

These cars were also extremely weighty, with the 5,500-pound starting weight of the ’66 convertible being only within around 8% of the starting weight of a new 2026 Navigator SUV (which weighs a full three tons), a much larger and much more usable vehicle.  It’s worth pointing out that the four-door hardtop weighed 400 pounds less than the convertible, and the hardtop coupe was 500 pounds lighter.  All of the structural reinforcement required for the convertible chop had to manifest itself in some kind of way.  In addition to its increased physical dimensions over the ’65, the Lincoln’s 430 cubic inch V8 was bored and stroked to 462 cubic inches, gaining 20 horsepower (340 vs. 320) in the process.

1966 Lincoln Continental convertible. Edgewater, Chicago, Illinois. Sunday, September 28, 2025.

Sales of the big Continental convertible had averaged about 3,200 annually from its introduction for ’61 through ’65, and about as many were sold for ’66.  The next model year would be the last for the drop-top Connie, but curiously, only about 2,300 found buyers.  (The convertible’s best sales year was ’65, with close to 3,400 units sold.)  Apparently, few Lincoln buyers cared that much that one of the most unique body styles among all vehicles for sale at that time was going away.  And thus, one of only a handful of factory-produced, four-door convertibles available for purchase since the end of World War II became a footnote in my automotive encyclopedia, but what a fine-looking automobile this Continental was and still is.

1966 Lincoln Continental convertible brochure pages, as sourced from www.oldcarbrochures.org.

Coincidentally, it was the first year of this design for ’61 in which the convertible had accounted for the highest percentage of total Continental sales, at 11% of about 25,200 cars, or just under 2,900 units.  By ’66 and despite an overall sales total that had increased dramatically thanks in large part to the introduction of a new, two-door hardtop which sold close to 15,800 units and also a $600 price drop for ’66 (about $6,000 in 2025) for similarly contented cars, the convertible accounted for just under 6% of that year’s overall tally of 54,800.

1966 Lincoln Continental convertible. Edgewater, Chicago, Illinois. Sunday, September 28, 2025.

For me, though, it all comes back to the sheer presence of the four-door Continental convertible.  To look at pictures of it somehow doesn’t do justice to its majesty when one sees one moving in traffic.  Suddenly, you feel like you’ve just witnessed the arrival and departure of a dignitary.  On the surface, anyway, this is exactly the way a luxury vehicle is supposed to make onlookers feel – like what and who they have just seen, however briefly, were larger than life.

Edgewater, Chicago, Illinois.
Sunday, September 28, 2025.

Brochure pages were sourced from www.oldcarbrochures.org.

Click the following links for reading on the 1966-67 Lincoln Continental convertible and also on the ‘65 Lincoln Continental.