I grew up in New Haven in the Hill Section and lived in a family house with my Grandfather on one floor.He lived there from approx 1916 to his death but in many conversations told me of driving across New Haven Harbor ,from the Smith Bros Oyster Operation( later the Chart House) over to Light House.While during my upbringing during many cold winters I saw partial freezing of the harbor but not to the extent of being able to drive an automobile on it.I believe these freezing experiences took place between World War One and World War Two.

The photo is showing Stony creek for the bonus

I do remember that during the 1960's there were the remains of an old car on Horse Island. On teen age picnics to Horse Island at that time we were all fascinated by it and always wondered when the sound had frozen over enough for someone to drive out there. It probably then thawed so the car wasn't able to be driven back to the mainland. Have no idea what kind of a car it was. Had I known it might have helped to put an approximate date on when it was that frozen. Must remember that cars were much lighter in those days but still heavy enough to require a good freeze.

I have discovered that LIS in different areas have been frozen 27 times not including 18,000 years ago when the glaciers covered this area with 3300 feet of ice.
http://cuppacafe.com/when-the-hudson-river-and-long-island-sound-froze-over/5845
http://en.wikipedia.org/wiki/Long_Island_Sound
http://wiki.answers.com/Q/Has_long_island_sound_ever_frozen_over
you look at these sites and make up your own mind In 1934 someone drove a car from Stony creek to one of the many islands in the Thimbles.

If there were a prize, Pete, you would win it! The image above is indeed a 1934 shot. One date down, two to go!

I kind of wonder if this car we are seeing is the one they drove out there and left it there since my uncle did say it was those dam young kids from Stony Creek

I have seen photos of the freezing over off Branford in 1977 Jan-Feb and I remember around 1963 Jan.

As for the weight for the car 4 adults and two children plus the car of about 1200 lbs the thickness of the ice would have had to been 8-12 inches. So knowing when lots of ice and snow is placed in salt water the salt content becomes lower it would have to be very cold for a long period of time to get that kind of thickness. On the other hand foolish folks like the ones in the photo might be posing on a rock formation frozen in the ice for the added weight. I remember ice fishing in the Branford River in 1963 and the ice thickness was about a foot in most places.

Alana one of the web sites I posted has the dates when LIS froze over another wayto find out for sure would be to ask the Coast Guard Historian in DC for the area they had to keep records but that site says 1963 In 1977 I was iced in at Governors Island NY with the ship I was on. We took Charlie status at the dock after our south patrol LIS was frozen and we didn't get out of NY till after Febuary

January 23, 1994, was a day for one of the peak experiences of my life - ice skating on Stony Creek Harbor. The whole Sound may not have been frozen, but that year it was solid out through the Thimbles. Most of it was broken up into jaggedy blocks of thick ice piled up on each other, but around Pleasant Point, it was miraculously smooth - just as good as on the ponds. At least six of us went out and skated up Pine Creek and around the end of the point, back and forth. The day was gray and pretty cold, and it was thrilling. We knew we weren't likely to do this ever again - even if it froze again, it would probably be too uneven for skating. Linda Zonana

I have photos (slides) of LI sound frozen in 1977. My friend and I walked out to Charles Island (on the ice) in Milford. The most interesting thing was that the surface of the ice looked like frozen waves.
The Sound was closed to all boat traffic for at least a couple of months.