The first time Dewey Livingston marched in the Western Weekend parade, he blended in with a group of young parents pushing strollers. They called themselves the Baby Boomers, and they wore T-shirts with a wailing infant on the front. 

Forty-two years later, Mr. Livingston has been selected as this year’s Western Weekend Grand Marshal. He will appear at the head of the parade, chauffeured alongside his two grandchildren, ages 7 and 11, who have…