Postmarked & Tipsy

Jessica and Kara
  • 5.0 (2)
  • Society & Culture

What can a postcard really tell you? On Postmarked & Tipsy, we explore real vintage postcards from the past — and the stories hidden between the lines. Each episode starts with a simple message… and quickly turns into something else: A mystery A question Or a story that doesn’t quite add up With a drink in hand, we dig into the details, the history, and the people behind the postcard — trying to figure out what was really going on.

  1. 2d ago ·  Bonus

    Postcards After Dark Episode 5: The Lollipop Graveyard

    🍭👻 A cemetery filled with giant white lollipops? Only in New England. Hidden in Harvard, Massachusetts, the historic Shaker burial ground contains more than 300 unusual cast-iron grave markers that look remarkably like lollipops rising from the earth. But behind this peculiar landscape lies the history of a religious community, a cemetery unlike most others, and local ghost stories that have attracted curious visitors after dark. In Episode 5 of Postcards After Dark, we explore the history behind the Lollipop Graveyard, the unusual markers and the folklore surrounding this fascinating New England landmark. Because every postcard has a story. Some should probably be read after dark. 🌙📮 Sources for this episode: - Harvard Shaker Lollipop Graveyard, Atlas Obscura, https://www.atlasobscura.com/places/harvard-shaker-lollipop-graveyard - Shaker Museum, https://www.shakermuseum.us/the-shakers - Harvard Historical Society, https://harvardhistory.org/topics/shakers/

  2. Oct 23 ·  Bonus

    Postcards After Dark Episode 4: The Whaley House — The Room I Couldn't Stay In

    I didn't go to the Whaley House looking for a ghost. I didn't even know there was supposed to be anything unusual about the room I walked into. Years ago, while in San Diego on a business trip, Kara used a free afternoon to visit the historic Whaley House. The tour began normally enough: history, architecture and stories about the Whaley family. Then Kara walked into an upstairs bedroom. Almost immediately, she was overwhelmed by a feeling she still describes as having a 50-pound coat dropped over her shoulders—an intense sense of dread, sadness and hopelessness. It was so strong that she turned to a complete stranger standing nearby and asked: “Can you feel that?” The woman could. Kara left the room without knowing why it had affected her that way. Then she went downstairs and mentioned what had happened to a woman in the gift shop. Her response? “Oh yes. Violet is in that room.” And that's when this stopped being an ordinary historic-house tour. 🌙📮 In Postcards After Dark Episode 4, Kara returns to her experience at San Diego's Whaley House, the tragic history associated with Violet Whaley, and the stories that have helped make the house famous for its alleged hauntings. Was what Kara felt paranormal? Psychological? Something about the room itself? She still doesn't know. But she knows what she felt before anyone told her what she was supposed to feel. And that's what has bothered her ever since. Every postcard has a story. Some should probably be read after dark.

  3. Oct 16 ·  Bonus

    Tavern Cold Reads Episode 2: Who Is Wanda, and What Happened to Cindy?

    One vintage postcard. Four amateur handwriting detectives. Absolutely no context. What could possibly go wrong? 🍺📮 For our second Tavern Cold Reads session, Raina and Richard return to the Tavern, joined by newcomers Dana Laverty of Rhode Island Monthly and Kara's cousin Rebecca. Their assignment? Decipher a nearly illegible handwritten postcard message without knowing the picture, date, postmark, sender's circumstances or recipient's identity. The message appears to come from a lonely woman named Wanda, who misses her familiar surroundings, hopes things will improve with the weather and mentions someone named Cindy who may—or may not—be causing trouble. Naturally, the theories escalate. Is Cindy a child? A puppy? A relative? Is Wanda trapped in a bad romance novel? And why does murder keep entering the conversation? But when we reveal the postcard's origins in 1966 Connecticut, the mood takes an unexpectedly emotional turn. Along the way, we discuss Catholic school penmanship, questionable family burial arrangements, launching ashes into space and our possible futures as bog witches. Murder. Loneliness. Seasonal affective disorder. We've got it all. 😂 Join us for another round of questionable deductions, historical rabbit holes and confidently wrong conclusions. And seriously… WHO IS CINDY?! 📮 Tavern Cold Reads is a special Postmarked & Tipsy series where guests attempt to unravel the mysteries of vintage postcards using only their handwritten messages. No Googling. No outside help. Just handwriting, imagination and occasionally outrageous speculation. Episode Sources: - The Lutheran Home Southbury website - Town of Southbury, CT website, including Southbury History by Joyce Hornbecker

  4. Oct 9 ·  Bonus

    Postcards After Dark Episode 2: The Rhode Island Teenage Vampire

    In 1892, residents of Exeter, Rhode Island, did something almost unimaginable today: they exhumed the bodies of three women from the same family, looking for evidence that one of the dead might be consuming the life of a surviving relative. The last coffin they opened belonged to 19-year-old Mercy Brown. What they found helped turn Mercy into one of New England's most famous so-called “vampires”—and Rhode Island into part of a much larger history of vampire folklore in 19th-century New England. But beneath the supernatural story was something very real: tuberculosis was devastating the Brown family, medicine had few answers, and frightened people were desperate to save someone they loved. In this episode of Postcards After Dark, Kara heads into the Rhode Island woods to explore the strange, sad story of Mercy Brown, the New England vampire panic, and what can happen when disease, grief, folklore and fear collide. And, because this is Postmarked & Tipsy, there's also the minor problem of what Kara found when she went looking for a vintage postcard of Exeter. 😂 🌙📮 Every postcard has a story. Some should probably be read after dark.

  5. Oct 9 ·  Bonus

    Postcards After Dark Episode 3: The Ghost of Hampton Court – Catherine Howard

    Centuries after Catherine Howard lost her head, people were still buying postcards claiming to show her ghost. In 1542, Henry VIII's fifth wife was executed at the Tower of London after a spectacular fall from royal favor. But according to one of Hampton Court Palace's most enduring legends, Catherine never entirely left the palace behind. Her ghost is said to haunt the gallery associated with the desperate attempt she supposedly made to reach Henry and plead for her life—a story that has become inseparable from Hampton Court's haunted reputation. Then, in the early 1900s, the story found its way onto postcards. Visitors could buy eerie images supposedly showing spirits at Hampton Court, including Catherine Howard—part ghost story, part early photographic trickery and exactly the sort of thing that sends Postmarked & Tipsy down a historical rabbit hole. In this episode of Postcards After Dark, Kara explores Catherine Howard's tragic story, the legend of her ghost, and the wonderfully strange era when supernatural tourism and postcard culture collided. And this one is a little personal: ten years ago, Kara visited Hampton Court herself—and naturally wandered around the palace wearing one of its green cloaks. Apparently, there were signs. 😂 🌙📮 Postcards After Dark is a special October series from Postmarked & Tipsy, exploring dark history, haunted places, folklore, true crime and the strange stories surrounding vintage postcards. Every postcard has a story. Some should probably be read after dark.

  6. Oct 2 ·  Bonus

    Postcards After Dark Episode 1: Chicago, July 1966

    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 going about her visit, one of the most notorious crimes in Chicago history was unfolding: the murders of eight student nurses by Richard Speck. In the first episode of Postcards After Dark, Kara follows the postcard into the history surrounding it – and considers something that makes old postcards particularly haunting: The people writing them had no idea which moments around them would eventually become history. The postcard isn't connected to the crime. And somehow, that may be the eeriest part. 🌙 Postcards After Dark is a special October series from Postmarked & Tipsy featuring short stories about dark history, haunted places, strange messages, vanished places and the unexpected stories surrounding vintage postcards. Every postcard has a story. Some should probably be read after dark.

  7. Sep 25 ·  Bonus

    Cold Reads from the Tavern: The Mystery of Mr. Bland and the Upside-Down Postcard

    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, postmark, location, sender or recipient – and were forbidden from Googling, consulting AI or summoning a professional handwriting analyst. Their mission: decipher the nearly illegible message, construct the story behind it and defend their conclusions—even if they turned out to be confidently wrong. What begins with an upside-down message leads to a 25-year absence, a mysterious trip east and a tantalizing reference to someone named Mr. Bland – or possibly Mr. Blonde. Then Kara reveals the address, postmark and picture one clue at a time. Was Eva returning home after a family estrangement? Did she run off to California with Mr. Bland? Did she escape him? And why did the Tavern’s theories eventually involve a missing body and a hotel fire? Pull up a chair. The Tavern is open.

  8. Aug 30 ·  Bonus

    A Quick Note from the Tavern

    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 a growing “Back to the Tavern” box filled with mysteries for Jessica’s return. Until then, 20 episodes are waiting for you—and Jessica’s seat at the Tavern will be waiting for her.

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Ratings & Reviews

5
out of 5
2 Ratings

About

What can a postcard really tell you? On Postmarked & Tipsy, we explore real vintage postcards from the past — and the stories hidden between the lines. Each episode starts with a simple message… and quickly turns into something else: A mystery A question Or a story that doesn’t quite add up With a drink in hand, we dig into the details, the history, and the people behind the postcard — trying to figure out what was really going on.

Information

  • Creator
    Jessica and Kara
  • Years Active
    2026
  • Episodes
    33
  • Rating
    Explicit
  • Copyright
    © 2026 Jessica and Kara