Paine Hollow and the Pond Hill School

South Wellfleet: Paine Hollow is easy enough to find, it’s a left turn off Route Six as you drive towards Provincetown.  If you do turn down the road, drive slowly, and imagine it as it was over one hundred years ago-  Greek Gothic-style farmhouses lining the road, and most of them owned by members of the then expanding Paine family. The road dead-ends at the water of  Loagy Bay and Blackfish Creek, where schooners were once moored. The following are some pages that were cut from the original preface of Eva and Henry, A Cape Cod Marriage, which was deemed “too long” by half of my volunteer readers. Here, the description of Paine Hollow as experienced by the main character, Eva Paine Smith:

“The neighborhood of Paine Hollow was self-sufficient and prosperous. Tidy whitewashed farmhouses and their companion barnyards spread like a quilt across the valley and down to the shore of the bay. As a little girl, I believed that everyone had as many cousins, aunties and uncles living close by. The feeling between neighbors was such that we would call a man “Uncle” out of respect, even if he wasn’t, and I was in my twenties before I unraveled the family tree enough to understand who my true aunts were and who had been bestowed the title through close friendship with the Paine family.

In 1792, my great-grandfather had come to South Wellfleet from the nearby town of Truro. Thomas Paine was attracted by Elizabeth Young, a grieving miss who had inherited a farmstead from her parents. It is said that Elizabeth was a beautiful bride, and her property was twice as attractive. Her house sat on a rise near the county road from which the terrain gently sloped a mile west down to the shore. Low hills bounded the bottom land on the north and south. The shoreline of the farmstead fronted on Blackfish Creek Harbor, which let out into the larger Wellfleet Harbor and thus provided convenient access to the main transportation lanes of the day—the watery realm of wind, tide and sail.

Thomas farmed the land and sailed his excess produce to market. He managed to scrape a living from his meadows—enough of a living to feed the many children birthed by the hardy Elizabeth. As their offspring came of age, Thomas generously sectioned the farm and gave a homestead parcel to each of his five sons and one daughter who survived to adulthood. Elizabeth loved her children and did not want them to settle far from her. She was rewarded by the great flock of grandchildren that lived within walking distance of her front door, my father being one of them—the seventh child of Elizabeth’s oldest son, Nathan.

A public road was laid out between the new homesteads and down to the shore, and a few parcels were sold to other families who recognized the allure of the location. It wasn’t long before the land alone could not sustain the growing number of hungry mouths living upon it. As always, the ocean provided. Navigation was taught as a winter subject in the local schoolhouse, and Thomas’s sons and grandsons called themselves seamen, not farmers, and sailed out upon the water.”

And so, Thomas Paine from Truro, MA (a son of the Thomas Paine who built the windmill now in Eastham) was the first Paine in the hollow. Thomas and Elizabeth’s sons all prospered and hired Zoeth Sparrow and Eldad Hopkins to build beautiful Greek-Gothic-styled farmhouses for their own families. The builders had a fine sense of balance and detail. The neighborhood was nominated and accepted for the National Historic Register in 1998.

Much of the research work was done by the late Elizabeth Cole, a granddaughter of a couple described in the book as good friends of Eva’s—headmaster Charles F. Cole and his wife, Lily Gray Wiley.

As Paine Hollow became more populated, it was clear that a school would be necessary. In 1857, Nathan Paine sailed a load of lumber down from Maine on his schooner and the neighborhood pitched in to build a school house. The boys and girls were taught on separate floors by two different teachers. In the winter, when the ice kept the older sailor boys home from ocean fishing, a “fishermen school” was held and complex navigation and reckoning methods were taught.

Once there were more than a dozen small schoolhouses in the town of Wellfleet; only the Pond Hill School remains, and it is now crying out to be restored. It has been cared for by the South Wellfleet Neighborhood Association. You will find the schoolhouse directly across from mile marker 100 on Route Six, just south of Paine Hollow.  Of course, the school house was built long before Route Six was laid out. It looks rather forlorn sitting up there on the hill, but if you are lucky enough to be in town on the night of a monthly potluck dinner, you will be amazed at the condition of the inside of the building. There are many features that remain intact. It’s worth a visit, and a donation to the restoration fund! Click here to see the school in its current state and check the calendar for events.  Please consider helping to preserve this slice of educational history.

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6 Responses to Paine Hollow and the Pond Hill School

  1. Bill Sulski says:

    Enjoyed the book greatly. Thank you.

    Our house is at the end of Pine Ave overlooking Drummer Cove. Of course we take walks along Paine Hollow road all the time. We are wondering if the homes discussed in the book are still standing? We are very close to the Pond Hill School, so the Smith home must be near us!

    Thanks again.

    • admin says:

      Yes, all of the houses are still standing. The Smith house was the first house on the right as you walk from the school on Old Paine Hollow Road and head north, towards Paine Hollow. Captain Otis Paine’s house is still owned by the surviving great-grandson, and is on the corner of Paine Hollow Road and Pleasant Point Road. Robert S. Paine (my father) has always been known as a collector. . . he cannot let go of anything that has been there for generations.So yes, the house with the purple shutters had all the treasures in the attic, revealing Eva’s life story. Abbot O. Paine, Jr- who just passed away last month at 90- of South Wellfleet, was Otis’s other great-grandson. He lived up on Route Six near the fire tower. Paine Hollow is listed on the National Historic Register as a historic neighborhood, and I believe at least six of the original Paine houses are still standing, and many are restored.

  2. ch and Betsy.....reading from Polly's in Vermont on Thanksgiving day 2010 says:

    Irene……are we/you trying to throw off the itinerant reader…the wandering roadster…..or the neophyte visitor to the outer Cape….in indicating that Paine Hollow would be to the right..hand…when driving toward P-town???? or a dyslexic typo…..

    we love you….hope you are recovering well….from Thanksgiving ….and surgery…..and finishing your wonder-full book……and hope to see you out and about….soon….love and light!ly….yr cousins…..from the Hollow….ch and betsy and deb and and and…..

  3. Lou Roy says:

    Hey Irene, I heard you were back in town. I hope that you are well. I plan to get a copy of your book very soon. I’ve gone to your web site and the website of, wonderful reading. I’m attempting to finish writing three grants to help preserve the hall that I still dearly love. Wish me luck and Thanks for the great read. Love to you, Jim, Natara (sp), your children, etc…. LOU ROY

    • admin says:

      Hi Lou- very good to hear from you. I am right here in Eastham. We could meet for tea! I’m glad you are working on the grants. Let me know what I can do to help. Irene

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