A Sail Back in Time

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Elizabeth Tilley (Photo Credit: Matt Villamaino)

Have you ever considered what everyday life was like for the Pilgrims? Some time ago, I joined a group of fellow Pilgrim John Howland descendants and set out for a late summer sail on the shallop Elizabeth Tilley in hopes of experiencIng one aspect of daily life in the Plymouth Colony.

It was a gorgeous New England September day when this small group of John Howland descendants set out for an afternoon sail on the shallop Elizabeth Tilley. After being ferried from Brewer’s Marine to the shallop, moored in Plymouth Harbor, our captain, Michael Goldstein, warmly welcomed his guests and offered a brief orientation to sailing aboard the Elizabeth Tilley in Plymouth Bay.

After this brief orientation to the shallop, the sails were raised and with much excitement we set out on our adventure. Leaving thoughts of the present moment behind, our imaginations led us into the world of a 17th century coastal tradesman. 

The Elizabeth Tilley is a reproduction sailboat from colonial times and our mind’s eye became filled with thoughts of John Howland plying his trade up and down the New England coast as the gentle sound of the bay waters lapped against the wooden sides of our workboat.

The sights and sounds of our crew managing the sailboat, as we sailed along-side an outcropping of sandy land called “the spit,” provided an introduction to how John Howland might have maneuvered his vessel through the tides and currents of Plymouth Bay so many years ago.

It’s true, we had the benefit of a motorized tender, but still the trip offered a glimpse into a world from many years ago. This was especially evident when the tender’s motor was disengaged and all was quiet except for the calming sounds of the gentle breeze against the canvas sails and the water rushing by our vessel.

For John Howland, sailing on the shallop, the trip through the bay would have been the beginning of a lengthy trip up the New England coast as he made his way north towards the Kennebec River in the northern reaches of the colony’s land grant. He and his crew were heading north to trade corn for beaver skins.

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Happy Sailors

For us, on this day, it wasn’t beaver skins that motivated the trip but rather a desire for a fun afternoon sail with family and the opportunity to better understand what colonial sailing might feel like. A gathering of the Waterman-Raybold family, all descendants of John Howland and a few other Pilgrims, came together for the afternoon sail.

As we entered the broader bay, our view of the town of Plymouth behind us offered us a deeper appreciation of the sight encountered by our forebears as they came upon the abandoned Indian village of Patuxet, nestled on the hill.

As we sailed on, we caught a glimpse of Clark’s Island and we were reminded of that frigid night when our ancestor, John Howland, and his Pilgrim companions, were shipwrecked on the island during a storm while investigating Cape Cod Bay and its surrounding inlets. Our sailing trip was indeed both an enjoyable modern outing and a trip back in time.

One highlight of the trip involved the opportunity to actually “man the tiller” and truly sail the Elizabeth Tilley. What a thrill it was to guide this wooden vessel through the seas. A number of cousins took turns at the tiller and each appreciated what it felt like to sail this shallop through the New England waters.

Our exciting trip back in time ended at our mooring in Plymouth Harbor with many eager hands taking down the sails, storing gear, and waving our afternoon good- byes. Sailing on the Elizabeth Tilley was a great privilege and thrill bringing us closer to the experiences of our Pilgrim forebears and closer to each other.

Have you ever been transported “back in time“ by an adventure you had with friends or family? Feel free to leave a comment below!

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Foredeck of the Elizabeth Tilley

Note: A slightly modified version of this article was previously published in The Howland Quarterly, The Compact, and The Mayflower Quarterly Magazine. Also, thank you to the Pilgrim John Howland Society for permission to use their photos. Follow Matt Villamaino on Instagram @mvillamaino.

10 thoughts on “A Sail Back in Time

  1. Hi Andrew, what a great post! It sounds like you had a wonderful time on that beautiful sailboat. Every time I go sailing, I feel like I am transported to another place. A place of calm and beauty, where it is just me, my little boat, and the wind the good Lord provides. Sailing is a wonderful experience! The sound of the water rushing by you, the feel of it comes up through your feet, as it travels under the boat. The sun on your back, or in your face, as the breeze caresses your skin. The feel of the tiller as she tugs against the tides and the wind. It is truly a remarkable experience.

  2. And you captured quite elegantly a row back in time and down memory lane. I am reminded of the trials and tribulations our forefathers encountered and the bravery they demonstrated as they forged the way for future generations. Thank you for this post.

  3. Always enjoyable, Howland cousin, to read your writing. Now you’ve whet my appetite to learn more about John Howland’s regular trips from Plymouth to Maine…give it a try please, to teach us what would have happened on the next leg of such a long trip to the trading outposts of the 17th Century in Maine (which of course wan’t officially “Maine” until 1820.) How long would he have stayed in Maine? What would he have brought back, furs to send to England, to pay off the Plimoth colony debts to their investors?

    1. Judy, Thank you for your warm comments! I’ll have to do some research and see if I can write something more about John Howland’s trips north.

  4. Morning Andrew!

    I loved seeing my mother in that photo and I’m so happy she was able to take that ride on the sailboat. Funny, I was down that way recently and thought it would be great to go for a sail on that boat. If you still have the contact info will you email it to me?

    The Block Island 40 will turn 49 this year and we’re looking forward to hopefully more sailing this year.

    – Janet

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