History, Mystery and Trains

A day out with Essex Steam Train satisfies an adventure

Whenever I take my sons out for an afternoon, we’ve always called it “our adventure.” Recently, these “adventures” have become errands to the store or getting haircuts. Not exactly what five and seven-year-old boys consider adventurous! I wanted to spark their imaginations and take them on a real adventure; one that they’d never forget.

I had a trick up my sleeve. Or rather, several tricks. Ways for all of us to have fun and experience Connecticut in ways that would be both surprising and, well, adventurous!

The secret? Trains, ferry rides, a castle, secret passageways, a tunnel, a riverboat and a bit of mystery thrown in. There was one way to get all of the above: the Essex Steam Train, specifically the Gillette Castle Connection.

Getting on board

Off the Train at Ferry RoadMy sons, Caleb and Benjamin, were “on board” the moment they heard we were going on a train ride. We made the drive to beautiful Essex and took some time walking alongside the vintage coaches before briefly exploring the historic 1892 train station. I lifted them up to peer inside the windows of the dinner train on the opposite track. “It looks like a fancy dining room, but inside a train!” Caleb had never seen the inside of a train before, let alone one with such detailed finery.

To the boys, trains are more of a curiosity than something they experience every day, so learning a bit about “how it once was” was eye-opening for them. We have toy train sets at home, but seeing and appreciating how massive steam engines are was mesmerizing for the boys.

We hopped onboard the historic passenger car to begin the rumbling six-mile trip up the Connecticut River. The conductor yelled “All aboard!” and the whistle of the searing steam signaled that our journey had begun. Our Essex Steam Train narrated tour helped us gain an appreciation for the history and beauty of this unspoiled area of our state.

The Valley route took us through tunnels of trees with wildflowers below. Around each bend, we found ourselves crossing a marshland as rivulets flowed into the mighty Connecticut. While Caleb counted bird sightings (112, 113…), Benjamin was probing a crew member on everything from the black Naugahyde seat coverings to that dining car he had seen earlier.

Waiting for the Chester-Hadlyme Ferry The train pulled into the Hadlyme Flagstop and we disembarked and walked down to the ferry landing. As the Chester-Hadlyme Ferry rumbled its way across the river, our collective gaze settled upon the same thing. There, up on a hill across the shimmering river, stood the uniquely beautiful Gillette Castle—the castle looked like it was built with the pillars from Stonehenge, crushed up and remolded into weird shapes.

Caleb marveled, “What is that?!” Benjamin suggested it was “a fort, like we play with at home!”

Viewing Gillette's Castle from Chester Hadlyme Ferry

As we got closer, the ferryman chatted to us about the history of ferries on the Connecticut River. He reveled in having such a rapt audience, and explained how the two ferries that cross the state’s longest river are two of the oldest in the entire country.

Pulling into the ferry slip, my sons’ eyes grew wide upon hearing about William Gillette’s former residence. Gillette was an actor who became famous for playing Sherlock Holmes, but his house contained as many mysteries as any Holmes tale! With secret passage ways, puzzle locks and all sorts of unique features, the boys were hooked.

Exploring a castle

Hiking to Gillette's CastleUpon docking, the boys practically ran up the incline to Gillette’s Castle, eager to get inside. As one of Connecticut’s cultural icons, I’d been here before. But seeing Caleb and Benjamin’s curiosity and wonder while staring up at the oddly constructed castle was a whole new experience. The eccentric actor made sure to have an equally eccentric home in which to live; there is no other house in the world like Gillette’s Castle. It has its own odd beauty, but Benjamin wondered aloud, “Why is this called a castle?”

“Shhh,” I said to him, “you’re about to learn all about this place!”

The docent was informative and patient. “Tell us about the secret stuff!” my boys asked. We learned all about William Gillette and his career playing Sherlock Holmes on stage. We were alerted to the trail network around the property, and how the main trail was a former train track that Gillette built to entertain guests.

Purchasing tickets for Gillette's Castle(No Benjamin, we won’t be building a train track in our backyard anytime soon!)

The woodwork and craftsmanship throughout the mansion impressed us all. Each door has its own hand-carved locking mechanism, and many of them are puzzling to say the least. The bannistered stairways and one-of-a-kind furniture pieces only add to the mysterious beauty of the castle.

Entering Gillette's CastleThe “secret” accoutrements fascinated the boys, especially the series of mirrors that allowed Gillette to see who was at his front door from his bedroom. Gillette was enamored with little tricks like this, and was constantly inviting friends to help him invent others. Even the light switches here are hand-carved and unlike anything we’d ever seen.

As we finished the tour, I could see the wheels turning in Caleb and Benjamin’s heads. They’d already learned about steam power, historic ferries and now one of the more inventive architectural gems in the region. I overheard them whispering about how they were going to invent a way to get out of their chores: “If we make some steam to power the robot, we can…”

Approaching Gillette's CastleI let them continue to plot in secret.

We walked the trails around the state park and found the old train tunnel Gillette had built through a hillside. As we entered, we could barely see the other end. Of course, the spookiness of the tunnel made it all the better. (It helped that dad was there to calm any nerves.)

We played “train” at one of the little stations Gillette built, but we had to catch the ferry back to the other side of the river. “Are you tired yet?” I asked.

“No!” came the rallying cry.

Riverboat cruising

I had one final card to play. The train made another stop at Deep River Landing and we hopped off again and immediately jumped on board the Becky Thatcher riverboat for a 1¼- hour cruise along the Connecticut River. I had never been on a boat like the Becky Thatcher, so this was a new experience for all of us.

The boat ride was a perfect ending to our day. We relaxed as we took in the natural beauty of Selden Island State Park and the Seven Sisters hills while blue herons fished at the riverside. Turning in front of the 103-year-old East Haddam Swing Bridge and the by the stunning Goodspeed Opera House only added to the ambiance. The Becky Thatcher brought us back to Deep River Landing and our connection with the steam train.

Connecticut River View from Gillette's Castle

After the short steam train ride back to the station, with conversations ranging from becoming detectives like Sherlock Holmes to dreams of longer hikes in Connecticut and wild inventions, I felt like “Dad of the Year,” even though it didn’t require much effort.


But that seemed ancillary at that moment. My boys and I had an incredible day out along the Connecticut River, learning many new things and play-acting scenes from days gone by. Those memories meant much more than any challenge could.

Buy your family’s tickets for Essex Steam Train’s Gillette Castle Connection.

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