Last updated: November 25, 2024
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Winter Holidays on the Boston Harbor Islands
Springfield Daily Republican, December 26, 1939.
Holidays on the Boston Harbor Islands had the potential of being cold, dark, and lonely. But residents of the Boston Harbor found community and light wherever they could. Enjoy some stories of how winter holidays were celebrated on the islands.
Flying Santa
It was the only way I had of saying 'thank you' to the lighthouse keepers and Coast Guardsmen. The boys in the lighthouse and Coast Guard service...were very helpful. I wanted to do something to lighten their loneliness.[1]
In 1935, Captain William Wincapaw gave this response when asked why he had started the tradition of "Flying Santa" six years prior in 1929. What began as a simple expression of gratitude to several lighthouse and Coast Guard stations in Maine, grew into an operation of reaching 91 lighthouses and Coast Guard stations across New England in just a few short years.
At first, Captain Wincapaw went on flights by himself, delivering bundles of presents, candy, books, periodicals, food, and other goods donated by community members. From his plane, Wincapaw dropped the packages over light stations, where they parachuted to safety below. The Morning Union observed a delivery in 1937: "Families waving greetings and thanks, their shouts of gratitude lost in the roard (sic) of Wincapaw’s plane, stepped out at the lighthouses to pick up the bundles."[2]
Boston Globe, December 12, 1948.
The flights soon included Wincapaw’s son, Bill, and later Winthrop teacher Edward R. Snow. Snow eventually took the reigns of the operation, expanding routes to cover the entire East Coast. Some years included the Great Lakes, West Coast, or even Bermuda. Snow's wife, Anna-Myrle, and daughter, Dolly, also participated in the operation. Snow brought holiday joy to remote lighthouse and Coast Guard communities for forty years.
Founded in 1997, the Friends of Flying Santa has continued the flights to this day.
Read more about the history of Flying Santa.
A Light House Family on Lovells
Harold B. Jennings, son of the lighthouse keeper for the Lovells Island Range Lights, remembered some unique holiday memories as a child growing up on the island.
In his memoir A Light House Family, Jennings recounted a Thanksgiving when they shared the meal with two British sailors. These sailors belonged to a ship in quarantine off the coast of nearby Gallops Island, and they had found themselves in distress while trying to fetch a soccer ball that had gone overboard. Jennings’ father directed them to safety on Lovells and welcomed them to Thanksgiving dinner until they could be picked up by the quarantine station later in the evening.[3]
Christmas was another special holiday celebrated by the Jennings family. Although they did not have electricity, the family still decorated the house for the festivities, including bringing in a cut white pine from somewhere on the island. During his early childhood, Jennings remembered Santa’s presents arriving via tugboat. When the Flying Santa tradition began in 1928, Jennings recalled:
As a lad, it was great to see Santa leaning out the plane door in his red suit waving a Christmas greeting, and then run after the parachuted package which would contain pencils, paper, coloring and story books, candy, gifts for the ladies and cigarettes for Dad.[4]
The Holidays at Harbor Forts
Matilda Silvia also fondly remembered the holidays in her memoir, Once Upon an Island. She grew up as a resident of Peddocks Island in the 1920s and 1930s, where her father had served as an army tailor at Fort Andrews.
Considered the first winter social event, Thanksgiving was held at the Barracks, where families enjoyed a dinner hosted by the Mess Sergeant.[5] Planning for Christmas also began in November. Children wrote letters to Santa while the community collected money from soldiers to buy presents. Silvia remembered her mother and other women created committees for caroling, buying gifts or treats for stockings, and organizing children for Christmas-related skits, recitations, and dance performances. After a holiday pageant on Christmas Eve, children met Santa and received presents from the Red Cross and Army personnel. Silvia also recalled the festivities on Christmas Day:
everyone was invited to the barracks for dinner. The mess hall would be decorated, and there would be a big Christmas tree for all to admire. There would be turkey and all the fixings, goodies of all kinds including candy, nuts, fruit, cakes and pies.[6]
In the 1940s, civilian organizations brightened holiday spirits for soldiers stationed at forts across the harbor. The USO and other groups organized dances, donated decorations, and sent gifts so soldiers could still celebrate, even if they could not leave the fort for the holidays. Even the Flying Santa (Edward R. Snow) "bombed" the forts of Boston Harbor, dropping gifts for soldiers stationed there over the holidays in 1940.[7]
Winter Celebrations at the Thompson Island Farm School
Students at the Farm and Trades School resided on Thompson Island (now also known as Cathleen Stone Island) year-round, including the winter months. In the early weeks of December, the students prepared for holiday festivities. In their workshops, they built gifts for family members. Band and choir students practiced for Christmas concerts. Collectively, they put up Christmas decorations in their buildings.[8]
Courtesy of the University Archives and Special Collections Department, Joseph P. Healey Library, University of Massachusetts Boston: Thompson Island collection
In the Thompson’s Island Beacon, student Charles L. Keller shared his experience of Christmas Eve 1924. The students stayed up until midnight "so as to get ‘Merry Christmas’ on the Instructors first." In the morning, the students opened their stockings and gifts. Keller found "an orange, a big bag of popcorn and peanuts, and a pack of dominoes" in his stocking that year. Customarily, the students received "bundles" from family members on holidays such as Thanksgiving, Christmas, and the Fourth of July.[9]
In addition to Christmas, the students on the Island rang in the New Year with celebrations. On New Year’s Eve in 1924, the students danced in Assembly Hall. Student Herbert E. Gove wrote that the students listened to the radio and "could hear music from Boston and New York" and enjoyed "cookies and lemonade for refreshments." On the first day of 1925, the students played hockey, basketball, and danced again in the evening.[10]
A Collection of Deer Island Holidays
Despite incarceration, inmates of the Suffolk County House of Corrections and The House of Industry held their own holiday celebrations on Deer Island. Officers granted parole for some to leave the island for Christmas, while others stayed on the island. In 1923, inmates celebrated with a show in the auditorium and enjoyed a festive dinner and "candies by the barrel." One inmate wrote about the joyous activities to the Boston Globe because he "wanted the world to know that the ‘boys behind the bars’ were not forgotten on Christmas."[11]
The Boston Globe
Even the smallest communities living on Deer Island held grand festivities. The City of Boston’s "smallest school" held their own Christmas play in 1928. All 12 students on the island performed "Toy Shop" with the help of their teachers. The play, accompanied by Christmas carols, followed the story of two children who fell asleep in a toy shop where the toys came alive at midnight. Parents, family, friends, and officers on the island attended the show. [12]
In 1930, rough seas prevented the Deer Island Lighthouse keepers from celebrating their typical Christmas. Unable to get to stores on the mainland for days, keepers Mal King and Jedson Small made do with what they had at Deer Light. Instead of a Christmas turkey, they celebrated with a feast of ‘Cape Cod turkey,’ or salt cod. Despite this, they kept their spirits high. Over the phone, Mal King said, "It’ll be Cape Cod turkey for us but we will have a merry Christmas anyway."[13]
Footnotes
[1] "Flying Santa Visits Lonely Light Keepers." Springfield Evening Union, December 24, 1935.
[2] "Yule Gifts Bomb Lonely Lighthouses." The Morning Union, December 25, 1937.
[3] Harold B. Jennings, A Lighthouse Family (Hingham, MA: Friends of the Boston Harbor Island, Inc., 2015), 102.
[4] Harold B. Jennings, A Lighthouse Family, 39.
[5] Matilda Silvia, Once Upon an Island (Cohasset, MA: Hot House Press, 2003) 31-32.
[6] Matilda Silvia, Once Upon an Island, 115-117.
[7] "Flying Santa Claus Will Visit Forts." Springfield Evening Union, December 11, 1940.
[8] Thompson's Island Beacon, volume 28, no.1-12, Thompson Island Collection at University of Massachusetts, Boston, https://openarchives.umb.edu/digital/collection/p15774coll3/id/306/rec/6.
[9] Thompson's Island Beacon, volume 1, no.1-12, Thompson Island Collection at University of Massachusetts, Boston, https://openarchives.umb.edu/digital/collection/p15774coll3/id/260/rec/6; Thompson's Island Beacon, volume 28, no.1-12, Thompson Island Collection at University of Massachusetts, Boston.
[10] Thompson's Island Beacon, volume 28, no.1-12, Thompson Island Collection at University of Massachusetts, Boston.
[11] "Inmate of Deer Island Tells of Big Time There Christmas," Boston Globe, December 26, 1923, 6.
[12] "Boston’s Smallest School Presents Christmas Playlet," Boston Globe, December 24, 1928, 4.
[13] "‘Cape Cod Turkey’ for Light Keepers," Boston Globe, December 25, 1930, 28.