The aircraft are Boeing P-26s, commonly known as the Peashooter. This was the first mass produced monoplane fighter aircraft built by a US Manufacturer. It was also the last open cockpit, fixed landing gear pursuit to serve with the US Army Air Corps.
The aircraft depicted in this painting are from the Bolling Field Detachment of Headquarters Command, so indicated by the fuselage insignia of the US Capitol
Army Air Corps. Pilots had to put in a number of hours monthly to earn their flight pay. I would expect these fellows, flying out of Bolling (which is approximately thirty miles from Tilghman Island as the crow flies) would come out over the Chesapeake to stunt, race and generally put their aircraft through various maneuvers. Since there were no height restrictions over water, I have a strong feeling that if these young men with fast airplanes spotted a Skipjack, they would, let's say, want a closer look! The year is 1934.