Postmarked & Tipsy

At first glance, there is nothing frightening about this postcard. It shows the Chicago skyline. On the back, Eileen writes about lunch with a friend, visiting relatives and good food—the kind of ordinary update people have mailed home millions of times. But then Richard, one of our Postmarked & Tipsy listeners, noticed the postmark. Chicago. July 1966. At almost the same moment Eileen was goi...

Cold Reads from the Tavern: The Mystery of Mr. Bland and the Upside-Down Postcard Regular episodes of  Postmarked & Tipsy  are currently on hiatus – but Kara cannot be trusted with free time and a giant stack of vintage postcards. For the first  Cold Reads from the Tavern , Kara sent Raina, Leah and Richard only the handwritten message from one postcard. They received no picture, date, postmar...

If you went looking for Episode 21 and wondered where the hell we went, Kara has a quick update from the Tavern. Jessica is very sick, and Postmarked & Tipsy is taking a little hiatus while she and her doctors search for answers. In the meantime, Kara shares her plans to keep the Tavern from going completely dark – including postcard field trips, listener-powered Cold Reads from the Tavern and...

“Don’t say anything.” Probably not the smartest thing to write on a postcard. In this episode, Kara and Jessica investigate a seemingly wholesome Thanksgiving postcard mailed from New York in 1912. But on the back, Julia has a secret: she told the folks she’d be in “the W”—but deliberately left out where she was really going. And she wants her friend to keep quiet about it.  Naturally, the theorie...

A postcard mailed from Glasgow on Oct. 27, 1911, carries a simple and unexpectedly sweet request: Arthur would be very pleased if his mother could visit while Auntie goes into the hospital. Naturally, Kara and Jessica still have questions. Why is Arthur writing when Uncle has already reached out? What exactly does he mean by inviting his mother to “have a look around”? Did she make the trip—and ho...

What happens when a vintage postcard begins with the words,  "Now you've gone and done it" ? In this episode of  Postmarked & Tipsy , Kara and Jessica investigate a 1982 postcard featuring an ancient Egyptian ibis mummy from the Virginia Museum of Fine Arts. The mysterious message mentions rising insurance premiums, someone named Judy who "didn't like him," and leaves us wondering one very imp...

What do Scottish fishwives, an unreadable postcard message, King Edward VII, and a Wild Berry Cosmo have in common? Apparently...quite a lot. This week, Kara and Jessica investigate a vintage postcard titled  Scotch Fishers' Washing Day , featuring women washing clothes along a Scottish stream—an ordinary moment that somehow became a tourist souvenir. Along the way, they try to decipher a mysterio...

A postcard mailed from Birmingham, England, during World War I turns into one of our favorite mysteries yet. In 1916, Flo writes to her friend Bertha, who's enjoying a holiday in Somerset, with one unusual request:  "Hope you will not fall in love with all the soldier boys—but save a few for when I come down." Naturally, we have questions. Every postcard leaves behind a few clues...and a lot of un...

This week we're heading home. Kara returns to Framingham, Mass., while Jessica shares memories from Lincoln, RI, as we explore two vintage postcards from the places where we grew up. Along the way, we revisit downtown landmarks, uncover local history, swap childhood stories, mix two hometown-inspired cocktails, and discover that even familiar places can raise unexpected questions. Every postcard l...

A postcard from 1911. One very confused writer. And someone named Teresa. This week we travel to Blackstone Park in Providence, Rhode Island, where an ordinary postcard raises extraordinary questions. Who was coming up? Who was coming down? And why does the writer remind everyone, "Not forgetting myself"? Along the way, we explore Rhode Island history, the Blackstone River, local landmarks, and a...

A 1947 postcard from Detroit leaves us completely baffled. Doug claims he doesn't know how to spell a word, compares it to another word he also can't spell, lists several foods he's apparently sick of, mentions a secret, and signs off with "Out of cards, love Doug." Naturally, we have questions. Along the way we explore Detroit history, accidentally fall into aviation history again, try a classic...

This episode has everything: - mysterious newsletters - someone named Miss Wrenchy - severed hands in a Christmas card - a possibly endangered turkey - Maryland Orange Crush cocktails - a “pink-spotted liar” #postcardquestionpodcast #postcardpodcast #postcardhistorypodcast #vintagepostcardpodcast #historymysterypodcast #postcardmysteries #oldpostcardstories #postcardquestions #hiddenhistorypodcast...

A postcard from 1941 mentions a mysterious “DeMolay Chapter” — and suddenly Kara and Jessica are investigating youth organizations, Knights Templar history, secret societies, and questionable slang. Also: - San Diego postcards  - Blue margaritas  - Karaoke debates  - Yosemite vs. the Grand Canyon  - A lonely night in Chinatown The postcards only get stranger from here. #postcardquestionpodcast #po...

This week’s postcards spiral quickly from “I need medicine” into wartime anxiety, mysterious boxes, diphtheria, and one deeply unsettling Christmas message. In this episode: - A desperate 1940 postcard from Kansas City  - The least festive Christmas card ever written  - A bizarre postcard coincidence involving “Master Karl”  - Rosé cocktails and creature double features  - Possible diphtheria zomb...

A century ago, an 18-year-old Massachusetts National Guardsman boarded a train bound for the Mexican border. At every stop along the journey, he mailed a postcard home. More than 100 years later, those postcards survived. In this special interview, Kara and Jessica sit down with Rhode Island Philatelic Society Vice President Shawn Pease to explore a remarkable family collection documenting one you...

A postcard from 1935.  A mysterious message.  A motorcycle insult.  And someone named Helen caught in the middle. In this episode of Postmarked & Tipsy, Kara and Jessica unpack a bizarre vintage postcard sent from Syracuse, New York during the Great Depression — complete with cryptic warnings, family drama and historical rabbit holes. Subscribe for more postcard stories, history and questions....

To our listeners - this is an episode best seen and heard because of the Boston 2026 World Expo visuals - head over to our YouTube Channel to watch it: https://www.youtube.com/@PostmarkedTipsy A few months ago, we were sitting in a Rhode Island tavern reading bizarre vintage postcards and trying to figure out what was actually happening in people’s lives decades ago. Then somehow… we got invited t...

In this episode of Postmarked & Tipsy™, we sit down with postcard historian, collector and educator Kathy Alpert to explore the strange, funny and unexpectedly emotional world of vintage postcards. What started as a conversation about postcards quickly became something much bigger: • why people once shared deeply personal thoughts through the mail • what postcards reveal about ordinary lives •...

Leading up to the Boston 2026 World Expo, we sat down with longtime broadcaster and former American Philatelic Society leader Lloyd De Vries to learn more about the fascinating world of postcards, stamps, postal history and collecting. We talk about everything from the Underground Railroad and Civil War mail to Queen Elizabeth’s Rolls Royce, Snoopy stamps, pneumatic mail tubes and why someone migh...

"I feel sorry for all you have to do… and no car to get around.” These postcards were sent to our guest’s family — and immediately raised questions. In this special guest episode of Postmarked & Tipsy, we’re joined by The Gallivanting Ginger, who explores abandoned places, roadside attractions, and historic sites across the East Coast. Together, we dive into two vintage postcards from the 1970...

We had questions about National Postcard Week… so we asked one of the organizers. In this episode of  Postmarked & Tipsy , we talk with Raina van Setter about the history of National Postcard Week, what people actually do during it, and why postcards are still relevant today. Music by  UnbanishedMule  from  Pixabay Keywords: Vintage Postcards, Postal History, Ephemera, Antique Postcards, Postc...

“We’re on our way… but we don’t know where we’re going.” In this episode of Postmarked & Tipsy, we explore a 1943 postcard from Carlsbad Caverns, New Mexico—and it might be one of the most unsettling yet. Subscribe for more postcard stories, history and questions. Music by  UnbanishedMule  from  Pixabay #postcardquestionpodcast #postcardpodcast #postcardhistorypodcast #vintagepostcardpodcast #...

“I thought you might like this for your collection…” In this episode of  Postmarked & Tipsy , a simple postcard turns into something unexpectedly layered. This postcard from 1940 shows Bridal Veil Falls in Oregon… but the message is about something else entirely. Subscribe for more postcard stories, history and questions. Music by  UnbanishedMule  from  Pixabay #postcardquestionpodcast #postca...

“Wouldn’t it be nicer… just family?” n this episode of Postmarked & Tipsy, a seemingly polite postcard reveals something much sharper underneath. Subscribe for more postcard stories, history and questions. Music by  UnbanishedMule  from  Pixabay #postcardquestionpodcast #postcardpodcast #postcardhistorypodcast #vintagepostcardpodcast #historymysterypodcast #postcardmysteries #oldpostcardstorie...

“We’re so sorry we didn’t see you Sunday…” In this episode of Postmarked & Tipsy, we read a postcard where: Ginny had a choice. Option 1: Spend Easter with her mother. Option 2: Drive to the mountains. She chose the mountains. Subscribe for more postcard stories, history and questions. Music by  UnbanishedMule  from  Pixabay #postcardquestionpodcast #postcardpodcast #postcardhistorypodcast #vi...