A couple of the Doolittle Raiders (one of them was Ted Lawson, who wrote 30 Seconds Over Tokyo) flying into Alameda to embark on the USS Hornet, flew their B-25s UNDER the Bay Bridge.
Doolittle, no surprise, apparently didn’t have much of a problem with his guy’s doing that.
Portland General Electric Co., of Portland, OR, used to employ a very talented and fearless ex-military pilot back in the 1970s. He would fly up the Columbia and Willamette Rivers under the bridges.
Richard Bong and 3 other P-38 pilots were reported to have looped the loop around the Golden Gate bridge in 1942. For that, and flying down Market Street below rooftop height, and a few other unauthorized bits of flying fun, Bong missed deploying to England with his unit, and eventually went to the Pacific where he became the top U.S. ace of WWII, with 40 victories.
Read the book as a kid and watched the move AGAIN three or four weeks ago on TCM.
B-25 flies under the Bay Bridge
Sequence begins at the 3:45 mark