Get Sleepy: "The Flying Lighthouse Santa" (December 17, 2025)

Episode Overview

In this festive episode of Get Sleepy, listeners are transported to the windswept New England coast in 1929, exploring the true story that sparked a heartwarming holiday tradition: the Flying Lighthouse Santa. The tale, penned by Elisha Stefan and gently narrated by Heather, pays tribute to the spirit of generosity and resilience within lighthouse-keeping families—and the extraordinary kindness of a local pilot whose small gesture blossomed into a century-long tradition.

Key Discussion Points and Insights

Life as a Lighthouse Keeper’s Child (08:39–15:00)

• Immersive Setting: The story begins by inviting the listener to imagine being raised as a lighthouse keeper's child in early 20th-century New England, waking each day to crashing waves, salty air, and the heavy, shared responsibility of tending the light.
• Hardship and Ingenuity: Life on remote island stations demanded self-sufficiency—families raised livestock, kept gardens in sparse soil, and innovated to survive long periods of isolation.
• Tradition of Creativity: Historical anecdotes (e.g., God's Rock Garden on Mount Desert Rock) show the community’s resilience and gratitude for small comforts amid adversity.

“Lightkeepers do not complain about their lives because they have chosen it... they know their work saves lives.”
— Narrator (Heather), 12:30

Christmas on the Lighthouse (15:01–20:00)

• Tough Holidays: The longing for togetherness and celebration was felt keenly at Christmas, despite handmade gifts, small pleasures, and family rituals.
• A Miraculous Arrival: Christmas morning unfolds quietly until a seaplane drops a mysterious parcel. The children rush to discover it—a simple package that becomes a symbol of hope and connection.

“The contents of the delivery are not extravagant, but they might as well be lavish gifts... The greatest gift of all is the thought.”
— Narrator (Heather), 19:30

The Beginning of a Tradition (20:01–27:00)

• William Winkapaugh’s Act of Kindness: On Christmas Day 1929, pilot William Winkapaugh dropped care packages to Penobscot Bay lighthouse families. His spontaneous generosity started a tradition that would span generations.
• Growing Appreciation: Overwhelming gratitude from recipients encouraged him to expand deliveries across New England.

Passing the Torch—Growth and Legacy (27:01–39:00)

• Family Involvement: Winkapaugh’s son, Bill Jr., and later high school teacher Edward Snow, joined the project—eventually delivering to as many as 91 lighthouses in a single year.
• Wartime Adaptation: During WWII, when the original pilots couldn’t fly, Edward Snow and his wife Anna Murrell took the reins. They even received heartfelt signs from families—like “Merry Christmas” spelled in newspaper—but also faced mishaps, such as broken packages or wayward landings.

“One lightkeeper’s wife spelled ‘Merry Christmas’ in newspaper; Ed was so delighted, he took a photo that made the local paper, completing the circle of appreciation.”
— Narrator (Heather), 34:30

• Memorable Rescue: In 1946, Snow hand-delivered a replacement doll by helicopter to little Simond Ponsart, after hearing her original had broken. This personal touch became a cherished lifelong memory for her.

“Ed Snow made my Christmases last forever.”
— Simond Ponsart (as quoted by Narrator), 37:30

Growing, Adapting, and Enduring (39:01–47:00)

• Packages Evolve: Over decades, sponsors added coffee, tea, toys, postcards, and feedback loops to improve delivery accuracy (94% success rate; the other 6%—often comically missed or mislanded).

“...the story goes, she called down to him directly, saying, ‘Yes, dear. We can start the party now.’”
— Narrator (Heather), on a package crashing through the skylight at Ipswich Light, 41:10

• Family Affair: Ed and Anna Merle’s daughter, Dolly, also joined the skybound delivery team, and as children grew up, new generations continued the legacy.
• Expansion: The tradition eventually spanned as far as the West Coast, the Great Lakes, and even Bermuda and Sable Island.

“Apparently, he once received a package a few weeks after Christmas that contained his fake white beard. With it, a light keeper had sent a note which read, ‘Here are your whiskers. Now where’s our package?’”
— Narrator (Heather), 46:20

Transition to Modern Times (47:01–51:00)

• Adapting to Regulations: In the late 1970s, insurance and FAA rules led the program to shift from planes to boats and helicopters, allowing more personal contact with recipients.
• Continuing Legacy: After the passing of Edward Snow in 1982, volunteers and non-profits like Friends of the Flying Santa kept the tradition alive—now focused on Coast Guard families as lighthouse automation increased.
• A Full Circle: In 2003, Simond Ponsart, recipient of that memorable doll as a child, returned as a Coast Guard member to deliver cheer to a new generation at her childhood station.

“57 years after Ed Snow had brought her a doll in a helicopter, Simond returned...to bring gifts to the Coast Guard children.”
— Narrator (Heather), 50:00

• Enduring Meaning: The episode closes with the reflection that while the solitary lighthouse keeper’s life has faded, the Flying Lighthouse Santa remains a testament to the importance of small, thoughtful gestures.

“The legacy ... shows us that it’s the little things, and most of all, the thought, that truly counts.”
— Narrator (Heather), 51:35

Memorable Quotes & Moments

• On duty & gratitude:
  “Lightkeepers do not complain...their work saves lives.” (12:30)

• On unexpected joy:
  “The greatest gift of all is the thought he had of sending you this package of holiday cheer.” (19:30)

• The “Merry Christmas” message from Ten Pound Island:
  (34:30)

• Simond Ponsart’s lifelong memory:
  “Ed Snow made my Christmases last forever.” (37:30)

• Humor amidst mishap:
  “Yes, dear. We can start the party now.” (41:10)
  “Here are your whiskers. Now where’s our package?” (46:20)

• Legacy reflection:
  “It’s the little things, and most of all, the thought, that truly counts.” (51:35)

Important Segment Timestamps

• [08:39] — Immersive scene-setting: Life as a lighthouse keeper’s child
• [15:01] — Christmas morning and mysterious airdrop
• [20:01] — Origin of the Flying Lighthouse Santa (William Winkapaugh)
• [27:01] — Expansion, family involvement, and wartime adaptation
• [37:30] — Simond Ponsart’s story
• [41:10] — Skylight incident at Ipswich Light
• [46:20] — Santa’s flying whiskers
• [47:01] — Shift to modern times, helicopters, and Coast Guard focus
• [50:00] — Simond Ponsart returns as a Coast Guard member
• [51:35] — Reflection: It’s the thought that counts

Summary Tone

Consistent with Get Sleepy’s gentle, reflective style—with soothing, evocative language and a focus on warmth, kindness, and the power of small gestures to create lifelong memories.

Conclusion

This episode of Get Sleepy beautifully retells a little-known chapter of American holiday tradition, intertwining history, compassion, and the enduring importance of thinking of others—reminding listeners that the smallest acts of kindness can cast light through even the darkest winters.