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OXFORD, Conn. — Dave Hamilton’s most notable flight was 75 years ago, when he was just 21 years old.

It was just after midnight on D-Day, and he was carrying 18 Allied paratroopers to the area behind Omaha Beach. The sky was full of planes that night as the young pilot encountered gunfire and nearly collided with a church before making his way back to England.

“I didn’t know a lot and boy, I learned in a hurry, I can tell you that,” said Mr. Hamilton, who grew up in Tuxedo, N.Y.

Mr. Hamilton — now 96 years old and living in Prescott, Ariz. — was back in a World War II troop carrier on Saturday, this time flying as a passenger in a formation flight over New York City with more than a dozen warbirds. The planes roared down the Hudson River and around the Statue of Liberty before returning for the night to Waterbury-Oxford Airport in Connecticut.