Vanderbilt Cup Races

To bad the video doesn’t have sound, that boat would sound great, loud I presume

From Willie K.'s "Hard Boiled Egg" Auto Boat

Great article! I appreciate the time you put into this. I work in a somewhat historic building off Stewart Ave and I was doing a little research into the history of the area. Thanks again! Keep it up!

From Long Island Motor Parkway Bridge Series #35: The "Meadowbrook" Bridge in East Meadow

Howard, a Super wealth of historical and educational information here produced by all, for all to benefit from. Kids learn best when they’re having fun. Please keep this forum going.
Frank

From Mystery Foto 2015 #1: Roosevelt Field and Roosevelt Raceway in July 1937 (Updated with a Then & Now)

You certainly got a lot of replies on this and good ones too. I didn’t even realize the ground was wet, I was trying to think where this was. You guys did a great job noticing things and I thought I was very observant, not this time

From Mystery Foto 2015 #1: Roosevelt Field and Roosevelt Raceway in July 1937 (Updated with a Then & Now)

I believe that is Roosevelt Field.  The building is Roosevelt Raceway. Initially created as a venue for motor racing but was converted to harness racing in 1940.

From Mystery Foto 2015 #1: Roosevelt Field and Roosevelt Raceway in July 1937 (Updated with a Then & Now)

Many guesses, with some researching to further complicate things. 
This post 1934 photo includes an auto race event at Roosevelt Raceway with cars trying to exit onto Old Country Road. And there’s the lining of aircraft outside maintenance hangars at adjacent Roosevelt Field.
This rear view angle of Roosevelt Raceway gives a much clearer perspective how immense the structure really was! The occupied observation tower on the left shows that there was an event taking place. The light attendance in the grandstand indicates the race is over. The exiting cars in the background are all facing north towards Old Country Rd and waiting patiently for the light to turn green. The cars in the foreground are parked in nearby Roosevelt Air Field for the maintenance workers. The race could have been the 1936 or 37 Vanderbilt Cup, or even the 1939 Midget Race held at the same location.
The DC-2’s maintenance was just completed in a hangar and needs to make room for other aircraft. It is being rolled out but not onto that flooded field. It will turn around and park alongside the older aircrafts. The DC-2 has a narrower body and shorter vertical stabilizer than its successor, the DC-3. The aircraft first flew on 5/11/1934, documentation here.
The Great Silver Fleet emblem was later replaced with Fly Eastern Air Lines. Eastern Airlines (one of the big four) under general manager WWI ace Eddie Rickenbacker, who had nearly monopolized U.S. eastern coast flights.
Guessing the bi-planes could be iconic Keystone B-5 bombers? I’ll leave those and the cars to the experts. I believe identification of the cars will get closer to the photo date. Motor Pkwy is running along the tree-lined stretch behind the raceway on the right of the photo, but impossible to see here. Waiting for the mystery answers and the final solution…….Happy New Year to all.

From Mystery Foto 2015 #1: Roosevelt Field and Roosevelt Raceway in July 1937 (Updated with a Then & Now)

Like I said before, this is going to be all guess work. This is before my time. I’m trying to think where a stadium and airfield was I can guess on a airfield, maybe LaGuardia Airport? As for the date, I’ll go with 1939, because of the years off the cars. On the aircraft, a DC3 and trainer planes.

From Mystery Foto 2015 #1: Roosevelt Field and Roosevelt Raceway in July 1937 (Updated with a Then & Now)

I believe the passenger plane is a DC-2 of The Great Silver Fleet of Eastern Airlines. The DC-3 engine nacelles look different. For the cars, I’ll go with a ‘31 Chrysler Coupe in front, a 36 Plymouth sedan, and a 36 Plymouth Deluxe Coach in back. The biplanes are either early Stearmans, before the ubiquitous PT-17, or they are Pitcairn Mailwings, which were used for air mail service. I believe the year of the photo is 1939, because there was a scandal about airmail contracts that was resolved a few years earlier, and the Great Silver Fleet was running in 1939. 1939 was also the last year of production of the DC-2. The photo could be as early as 1936. Eastern was flying from Newark, but if this is Long Island, it is probably Glenn H. Curtiss Airport, now known as LaGuardia. I have no idea about the structure in back. It looks like a grandstand.

From Mystery Foto 2015 #1: Roosevelt Field and Roosevelt Raceway in July 1937 (Updated with a Then & Now)

What kills me is that I used to take that corner regularly (and rapidly - traffic signal allowing) ca. 1976-90 (and before and since) and never realized it was Colyer’s!  Thanks, as always, Howard.  Sam, III

From From the Luttgen Album: Driver Foxhall Keene Taking the Turn at Colyers Corner in Plainview

-Identify the location
Roosevelt Field/Roosevelt Raceway

-What is the approximate date of the photo? Provide a rationale.
Early 1940s - Eastern Airlines operated DC-3s as part of their Great Silver Fleet in the early 40s.  Also if I’m correct about Roosevelt Field, it operated at that time as a civilian airfield before the US military used it during WWII.

-What is the large structure in the background?
Roosevelt Raceway grandstand

-Identify the three automobiles and three airplanes in the foreground.
Only answer is the above mentioned DC-3. 

From Mystery Foto 2015 #1: Roosevelt Field and Roosevelt Raceway in July 1937 (Updated with a Then & Now)

Roosevelt Field.  1937 because of the Raceway grandstands and banked track.  Looks like Fleet Model 2s with Kinner K-5 radials, probably belonging to Roosevelt Flying Service, like the one George Dade flew and restored (hanging in the Cradle of Aviation Museum) - whoops - wrong - different rudder and landing gear strut.  Sorry to disagree with the great Janet Guthrie but that’s an EAL DC-2 (NOT -3); seven side windows; early DC-3’s only had six; but the kicker is the jog in the vertical fin and rudder!  I flew in a -2 from LaG to DC in one in 1941.  The car in front is a 1932 (twin bumpers with curved upper bars, straight grille, and external horns) Chrysler 6 (short hood); the other two are ordinary Detroit iron.  Sam, III

From Mystery Foto 2015 #1: Roosevelt Field and Roosevelt Raceway in July 1937 (Updated with a Then & Now)

That’s a photo taken at Roosevelt Field looking southeast from either the roof of one of the hangars or an upper window. It is probably from 1936 as the structure in the background is the grandstand for Roosevelt Raceway, built for the 1936 & 1937 Vanderbilt Cup Races. The two bi-planes are Curtiss “Fledglings”, also known as Curtiss models 48 or 51. They were used primarily by the US Navy as trainers who called them “N2C’s”. The larger plane is probably a Douglas DC-2 since Eastern Airlines only started using the slightly larger DC-3 in 1935. As for the cars, I think one might be a 1935 Plymouth but they all look like the same black box to me. No other guesses.

From Mystery Foto 2015 #1: Roosevelt Field and Roosevelt Raceway in July 1937 (Updated with a Then & Now)

There were at the very least two because of the perforated cross-member under the radiator, as I had noted in a much earlier post.  I find it difficult to determine wheelbase but there were clearly shorter and longer models.  Details such as brackets and wheels and such are easily changed during the life of a car.  Ariejan is spot-on about the D-B Archive; I have found them immensely cooperative and helpful.  Sam, III

From The Unsolved Mystery of William K. Vanderbilt Jr.'s 90-HP Mercedes Automobile(s) (1904-1908)

(Coincidentally, I just read an article about the history of Eastern Airlines last week!)

It appears to be Roosevelt Field.

I’m thinking it is either the 1936 or 1937 Vanderbilt Cup race, although the rain is making me consider that it could have been 1938 when there were hurricane relief flight coming into Long Island using Douglas aircraft.

Roosevelt Raceway and grandstands in background.

I pass on the automobiles.  With the ultimate respect for Janet’s answer, I believe that the airplane is actually an Eastern Airlines DC-2 judging by the rudder hinge shape and lack of a color stripe down the side in the paint scheme.  Eastern bought 10 of them in 1934-1935, and sold the lot to Australia in 1941 for military use since the DC-3 had 3-row seating (21 passengers) versus the 14-passenger DC-2.  I wish that the registration tail number was visible!

Since Eddie Rickenbacker was actively involved with re-starting the Vanderbilt Cup Race at Roosevelt Field and also served as head of Eastern Airlines during this time period, it seems plausible that he was using one of their DC-2’s as transportation to the race for himself and/or other VIP’s…..

From Mystery Foto 2015 #1: Roosevelt Field and Roosevelt Raceway in July 1937 (Updated with a Then & Now)

I agree with Janet about the DC-3, (in military use it was called it a C-47 I believe) I would date the photo about 1938 as in the distant back ground group of cars there seems to be a Chrysler product sedan from that year. The cars in the foreground are 1931 or 32 Chrysler 6 cyl. coupe, 1935 DeSoto sedan, and a 1935 or 36 Pontiac 6 cyl. sedan. The structure at the distance is the grandstands for the Roosevelt Race way.

From Mystery Foto 2015 #1: Roosevelt Field and Roosevelt Raceway in July 1937 (Updated with a Then & Now)

The Old Court house Bridge should be a definite landmark, as well as that stretch of the parkway .  Artie.

From VanderbiltCupRaces.com Polls (New Poll: April 13, 2026)

I am glad to see that Old Westbury Gardens is the winner, as Chief Judge last year I can tell you It’s a lot of work and I am glad to see it appreciated by fellow car owners.We had over 500 cars hope to see the Chrysler there next year.  Artie.

From VanderbiltCupRaces.com Polls (New Poll: April 13, 2026)

Hi Howard—

I can only do one, but that is an Eastern Air Lines DC-3. I would say approximately 1939; I think Eastern ordered its first DC-3s in 1938. My father flew them from the time he joined Eastern Air Lines in 1941.

I thought the airplanes might be the ubiquitous Jennys, the WWI JN-4 trainers, but apparently not.

Last time I rode in a DC-3 was in Haiti, in about 1970, from Cap Haitien to Port-au-Prince. Beat the heck out of a tap-tap passenger truck that I’d taken on the way north.

Best,
Janet Guthrie

From Mystery Foto 2015 #1: Roosevelt Field and Roosevelt Raceway in July 1937 (Updated with a Then & Now)

Location: Roosevelt Field
Date: July 1937.  It appears to be a crowd for a special event, like the Vanderbilt Cup Race
Background: The Roosevelt Raceway grandstand
Autos left to right: ‘36 Pontiac, ‘36 Chevy, ‘32 Dodge
Airplanes: (2) Stearman army biplanes
The large aircraft appears to be an Eastern Airlines DC-3

From Mystery Foto 2015 #1: Roosevelt Field and Roosevelt Raceway in July 1937 (Updated with a Then & Now)

Location Roosevelt field airport
About 1931
Roosevelt raceway
Large plane DC-3
Biplanes Curtis
Autos Franklin dodge chrysler

From Mystery Foto 2015 #1: Roosevelt Field and Roosevelt Raceway in July 1937 (Updated with a Then & Now)