Portland Main Post Office

About this location

A few stories people tell about this place

1. One morning, a delivery driver noticed something odd in the mail sorting area—a small envelope addressed simply to ‘The Loneliest Heart.’ Curiosity piqued, he opened it and found a handwritten note inside: ‘Dear Portland, I miss you already. Love, Your Favorite Neighbor.’ The next day, another letter arrived: 'Dear Portland, I'm back! Missed our conversations.' The driver chuckled, thinking maybe someone was playing a prank. Then he saw more letters pouring in—all addressed to 'The Loneliest Heart' from different neighbors around town. It turned out that Portland had become an unexpected pen pal for everyone.

2. In Portland’s old Main Post Office, a regular would often see an unusual sight during lunch breaks. A small pigeon, seemingly unafraid of humans, would perch on top of the mailboxes and peck curiously at envelopes before flying off with a piece of paper clutched in its beak. One day, a delivery driver noticed the same pigeon carrying not just any envelope but one addressed to himself. Curious, he followed it down the street until it landed on his neighbor’s balcony. Turning out, the note was a handwritten invitation for coffee—an anonymous gesture that brought joy to many locals.

3. Late one night, a postal worker was closing up the Main Post Office when he heard a strange noise coming from the ceiling. Curious, he climbed up and found a tiny envelope stuck between the beams—addressed simply to ‘The Night Letter Carrier.’ He opened it carefully, only to find another note inside: ‘Dear Night Letter Carrier, please deliver this letter to yourself.’ Inside was an old chocolate bar wrapped in foil. The worker smiled, thinking it must be a prank from a regular. He popped the candy into his mouth and went home, humming softly.

4. In Portland’s old Main Post Office, every afternoon around three o’clock, a young boy named Timmy would visit the mailroom. He’d stare wide-eyed as the mail sacks were sorted and bundled, until one day he pointed excitedly: ‘Look! The letters are dancing!’ One day, an elderly delivery driver noticed Timmy and asked curiously, 'Do you always see dancing letters here?' With a serious nod, Timmy replied, 'Only when it's almost closing time.' The driver chuckled and whispered back, 'That's because they’re just shadows on the wall from the setting sun.' From then on, whenever anyone saw Timmy in the mailroom, they knew it was nearly quitting time.