Brattleboro letter carrier Viv Woodland displays a 1921 postcard at its intended address after its mysterious century-long journey across the country. Photo by Kevin O’Connor/VTDigger

BRATTLEBORO — Town letter carrier Viv Woodland knew something was strange the moment she tried to deliver the postcard.

It wasn’t simply that the person it was penned to, Holland L. Smith, didn’t live at the listed Brattleboro address. The color of the sunny California orange grove on the flip side looked more like sepia. The stamp was purchased for a penny rather than the current 44-cent rate. And the postmark seemed to be a year old — from ’21.

On second look, make that 101 years old — from 1921.

So begins the story of a head-scratching postcard and what the family of its late recipient hopes people will see as its larger message.

It all started March 28, 1921, when a telephone operator named Lena bought the card that pictures the succulent city of Pomona, California, framed by a backdrop of frosty mountains.

“How would you like to pick a few oranges today,” she wrote in black ink on the back. “It was 85 in the shade this noon and the mts. are covered with snow. The wind is blowing a perfect gale and at San Bernardino they are having a big sandstorm.”

Addressing the card to “Holland L. Smith, 24 Oak St., Brattleboro, Vermont,” she then placed it in the mail, according to its 1921 postmark.

Some 2,863 miles away, Smith was a 14-year-old ninth-grader at Brattleboro High School living in a duplex full of family — including his grandmother, who had adopted Lena as a baby.

Graduating from high school in 1924, Smith earned a bachelor’s degree in history from Colgate University and, after joining the Navy during World War II, a master’s in education from the University of Vermont.

Smith worked as a radio sportscaster, newspaper correspondent, teacher and track coach before serving as principal of Burlington High School from 1950 to 1964, assistant superintendent of schools from 1964 to 1971 and a member of what’s now the Burlington City Council from 1946 to 1952 and 1964 to 1968.

Holland L. Smith as pictured in his 1924 Brattleboro High School yearbook. Photo by Kevin O’Connor/VTDigger

When Smith died in 2000 at age 94 — leaving four children, 14 grandchildren and 16 great-grandchildren — the Burlington Free Press called him “Mr. Everything.”

Fast-forward to this fall, when Woodland found a card in her delivery bag with two postmarks: The first from Pomona in 1921, a second on the other side reporting, “Sacramento CA, 20 Oct 2022.”

The carrier can only speculate about its whereabouts over the past century.

“It may have traveled and made its way back to California somehow, such as through a relative’s belongings, or it could have been hiding for 100 years under a piece of equipment in a postal facility,” she said. “Generally, an undeliverable postcard with no return address such as this would be sent to the ‘dead letter’ facility, but I wanted to give this piece of quotidian history a chance.”

With some sleuthing from a reporter on her route, Woodland learned all four of Smith’s children still live in Vermont — Nancy Smith Tracy in South Hero, Sally Hackett in Shelburne, David Smith in Huntington and Debbie Bedrin in Grand Isle — and the latter has a newborn grandson with the middle name of Holland.

They, in turn, helped piece together the rest of the puzzle.

“This happy ending is better than I could have imagined,” Woodland said.

The carrier put the postcard in an envelope and mailed it to Smith’s eldest child, Nancy. The 90-year-old and her siblings, having just received it, know they could gripe about the century-long delay in delivery. Instead, they’ll gather this Thanksgiving to express something else: Gratitude for a sunny, succulent memory springing back to life.

VTDigger's southern Vermont and features reporter.