October 17 2023

Cuttyhunk Island | My Best Lesson

by Jake
38 comments

This post was originally published in June of 2017.

My teaching career began many years ago. I was a young man being trusted to educate 7th graders at Plymouth Community Intermediate School.

This task consumed me. 

I struggled during my first year to make Social Studies come alive. One of the units I taught was about local history.

We spent lots of time studying the history of the Cape and surrounding areas. This was very exciting to me but, sadly, not to my students.

One Sunday afternoon I took my wife Kathy, son Ryan, (age 4) and daughter Katelyn, (age 3) on a fishing adventure along the coast of Cuttyhunk Island.

Any parent will tell you that keeping young ones interested in fishing while not catching is a real challenge!

The author, Jake Collins, with his two children, Katelyn & Ryan, on a trip to Cuttuyhunk during the early 1990's.

So I soon gave up on the fishing and went into Cuttyhunk Harbor, and tied up the boat for a few hours.

Cuttyhunk Harbor/Pond circa early 1990's.

I let the kids run and we explored.

As luck would have it, I met the island teacher, Ellie Siefert. We began talking about our respective schools and students.

The author & his family in front of Cuttyhunk's one-room schoolhouse. Pictured in the background is Cuttyhunk's sole student at the time - John Paul Hunter. John has since returned to Cuttyhunk and operates a water taxi service between the island and mainland.

My school in the town of Plymouth had 2000 middle school students and Ellie's school had one seventh grader, John Paul Hunter, and his dog.

That's when I had an epiphany - a student "Exchange Program" between Cuttyhunk and Plymouth.


The Cuttyhunk Exchange Program

(my best "lesson")

125 middle school students and chaperones from Plymouth, MA gather outside Cuttyhunk Island's picturesque 1 room school house.

Ellie and I communicated for months in order to bring a Cuttyhunk-Plymouth exchange program to life.

In early Spring, the island's only student, John Paul Hunter, arrived with Ellie as my guests at my very large middle school in Plymouth MA.

The local newspaper loved it, and John could not believe the number of girls in my school. We were then invited to visit John's one-room schoolhouse on Cuttyhunk Island.

In late May I chartered the Captain John boat out of Plymouth with my wife Kathy, my kids Katelyn & Ryan, and 125 seventh graders and chaperones.

Leaving Plymouth harbor and continuing through Cape Cod Bay, transiting the Cape Cod Canal into Buzzards Bay, we finally reached Cuttyhunk Harbor in 3 hours and 15 minutes.

John and Ellie met us at the dock and gave us a grand tour of the school and island followed by a cookout.

My students and staff all agreed that this was, by far, my best "lesson". 


Retirement from Education

As of today October 17th, 2023, I have been retired for 13 years and enjoy a slower pace. It is hard for me to believe that 31 years has gone by since my "best lesson" at Cuttyuhunk Island.

My son Ryan is now 38 years old and will stay up for days fishing-especially when he visits the shoreline of Cuttyhunk to surfcast for stripers.

I can no longer keep up so I've since picked up less strenuous nautical jobs, first with Freedom Boat Club and now as a fuel dock attendant at the Sandwich Marina.

I enjoy it!

It's a nice Cape Cod retirement gig.


My Return to Cuttyhunk

Back when I was still working at Freedom Boat Club, I liked to take full advantage of the gig.

One day when conditions were perfect, I borrowed one of the boats and left Kingman Marina in Cataumet, en route to my old stomping grounds of Cuttyhunk.

Cruising at a comfortable speed I arrived at the island in what seemed to be no time at all.

Amazingly, the boat behind me was John Paul Hunter's water taxi - the Seahorse!

John Paul Hunter, if you recall, is the man who was once the only student at Cuttyhunk's one room school house.

We met at the dock and reminisced.

Of course I had to re-visit Cuttyhunk's famous one-room schoolhouse.

I remembered how we filled that small schoolhouse with 125 middle schoolers on that special day some 31 years ago.

I then walked up Cuttyhunk's famous hill.

I could not help but reminisce about the time two decades ago when I walked this same hill with my then 3 year old daughter Katelyn crawling behind.

Two hours later I departed the island, and carefully explored the area of Robinson's Hole.

One must be careful and keep a close eye on your GPS chart when navigating the waters of Robinson's Hole, and around the Elizabeth Islands.

There are many rocks and swift currents to be aware of.

Be sure to also keep a close eye on the wind, especially the southwest wind which usually kicks up during the afternoon in the summer.

I also took a quick dip at West Beach which is always great.

I then cruised back by Bassetts Island and entered the harbor at Kingman Marina.

Kali, part of the Freedom Boat Club's dock staff, greeted me and asked about my day.

My response was that I had revisited my "Best Lesson". Kali appeared to be a little confused, but as always she did a nice job helping to dock the boat and secure the lines.

In conclusion, John Paul and my students of 1989 were exposed to extremes such as hands on and authentic learning. They will never forget the Cuttyhunk Exchange experience and neither will I.

Tight lines 🎣

-Jake

About the author 

Jake

Boating has been part of my life since I was a boy hand-lining for mackerel from a dinghy. When Ryan of MFCC was young, we'd spend our days fishing from our 12ft tin boat. Today I still enjoy boating with Ryan, my daughter Katelyn, and my lovely wife Kathy.


  • Hi Jake,
    This Spring my fishing partner Ned Bean and I stayed at The Bass Club for three days as we surfcasted our favorite old man spots around the Island. I reenacted one of the photos inside by covertly bringing it out to the back porch and having Ned take a photo of me in the same spot and angler pose with the original as a backdrop. A bit eerie and wondering if I would enter a time portal back to the 1900’s!
    We had breakfast at the Club and our server was Gwen, the last student at Cuttyhunk Elementary. I remember seeing her and her brother Carter playing outside of Pete’s Place the first time Ryan brought us to Cutty.
    Gracie says Hi!

  • Hey Jake, I just stumbled upon this story. A very enjoyable read! A beautiful experience and memory for you and your children. Great Blog! Love the pictures!

  • Jake,

    Great story and glad you were able to reconnect with the island and JP.
    I really enjoy this page and appreciate your son and you sharing your experiences and love for striped bass fishing and experiences on Cuttyhunk.
    I spent at least one week a summer on Cuttyhunk from the time I was born through college.
    My dad was a teacher as well and taught me how to surf cast for stripers as when I was about 12 years old in the summer of 1986 from the rocky shores of Cuttyhunk. My dad spent all his summers on Cuttyhunk as a kid. JP is my cousin and a great guy.
    I am looking forward to our annual trip to Cuttyhunk this week and have finally invested in my own set of surf casting gear so I can teach my 8 year old son to fish this summer!
    I have been reading MFCC these past few months in an attempt to figure out what techniques, tactics and procedures will work best for surf casting in July.
    Thanks again and hope to meet you guys someday.

    Semper Fidelis,

    JJ Bancroft

    • Thank you for reading, J.J. You must have really enjoyed your time on Cuttyhunk. Now you can bring this passion to the next generation. I loved it when my son was your son’s age and introducing him to new adventures. I would let both of my children have the run of the island. The fieldtrip that I put together was the most rewarding event of my career. John Paul is a star on the My Fishing Cape Cod website. I seem to run into him every time I visit the island. Have a great vacation and give my best to JP. Jake

  • I loved reading this article! And I was on Cuttyhunk on June 24,25 (as well as 5 other overnights on my sailboat this season!) I too was a teacher and as part of my 10th grade geometry course, I taught a 4-day course on applying geometric concepts to navigation and concluded by chartering the New Bedford ferry and having my students plot their course all the way to the island. They rated this field trip the best in their 4 years of HS! And they were fascinated by the one room schoolhouse. Your friend, Marianne Baird, sent me this article. We were college roommates. Thanks for the article and the great pics!

    • Thank you Denise. Great learning for our students. Hope to see you on Cutty some time. Look for my face with the big smile. Thanks for reading, and have a great summer. All my best.

  • Hi Jake !
    Wow! What a wonderful story / reflection on your journey with Cuttyhunk Island over the years. The photos really bring it to life too. You’ve given so many memories to your students and family that they will take with them for a lifetiime. I remember your love and passion for the Island.
    Congrats on the job with freedom Boat Club! They are in good hands with you! May God continue to bless you in your retirement!
    Marianne & George

  • Great story Jake, thanks for sharing. I was one of the lucky parents. You taught my son, he speaks fondly of you. You are a great educator.

  • Jake, that was a very sweet story, with sweet memories, for sure. It took me a minute to realize it was you, and Ryan as a youngster. Even though I don’t ever seem to catch much there, Cuttyhunk has special memories for me during my time here in MA. Someday I hope to go there by boat, too, and travel through the Elizabethan islands.

  • Loved reading this Jake! Such a positive story of learning – for the students and for you. Of course it tugged at my heart a bit. Sometimes we don’t realize the passage of time until we remember one specific incident and then revisit it. I’m happy you’re finding such fun and interesting ways to fill your retirement!

  • This was great! I’ve always wanted to go over there and never have, maybe this summer! Sad my class didn’t have the opportunity to experience this trip with you, sounds like it was fun! Thanks for sharing!

    • Thank you Jackie. You need to put this on your bucket list. Two boats leave New Bedford for Cuttyhunk. Google Cuttyhunk for info.

  • This was great Jake. I especially liked the picture comparison of then and now. This was a good bit of information on Cuttyhunk, as I rarely find enough info to know what to expect. Ryan’s intro to the National Seashore trip, with pictures of the old aluminum boat, was enough to inspire me to get one. I’d actually be interested in hearing more about fishing from your little boat (i.e. where you’ve taken it, and any tips you might have).

    • Hi Brian, Tin boat is fun and safe at Sandy Neck, Barnstable Harbor, Scorton Creek, and all Cape tributaries. Small fish on light gear with soft plastic works well. Might even get a big boy. Once a tuna chased my catch. True story Ryan was with me as it went under the tin boat in 15 feet of water. Like with any boat keep an eye on weather. Enjoy.

  • Hey Jake,
    Adorable photos of the kids, very cute. I think Katelyn is on to something with her way of getting around Cuttyhunk. I have felt like crawling many times after hours of walking the rock filled beaches of Cuttyhunk.
    I can totally relate with being consumed in your quest to make your lessons exciting for your students. I call it the “ooh ahh” factor.
    Glad that you found such a great job that fits your talents and interests!

  • Thanks for the great story Jake. When you said that you were there in the 1990s, I thought to myself that’s not too long ago, but actually it’s getting close to 30 years ago! Wow time flies.

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