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Gillette Castle and Chester, CT

Gillette Castle and Chester, CT
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Gillette Castle in East Haddam, Connecticut, is amazing. From a distance, it looks like a medieval sand castle, dribbled on top of a cliff.

Did you ever turn a corner and suddenly feel like you’ve driven off the map? Discovered your own little patch of unspoiled turf?

Off the map...
Off the map…

It’s happened to me in Spain once or twice, and Scotland, too, backing up on a long dirt road. Where I got the feeling, just for a second, that nobody else knew about this place. How great is that.

Weirdly, I had that sensation driving into Chester, Connecticut.

Along Main Street... Along Water Street…

And while that is so clearly NOT the case—Chester’s only a couple of hours from NYC by train, after all—the beauty of this little burg is that it succeeds in giving that impression.

Some lucky artist's burrow... Some lucky artist’s burrow…

While at the same time serving up robusto cappuccino and dangling some nervy little shops and restaurants at your pocketbook. Plus there’s a cool ferry just minutes from town that crosses the Connecticut River and drops you at the foot of a crazy, Gaudi-like stone castle teetering on the tip-top of a precipice.

Gillette's Castle Gillette’s Castle

Pretty fine entertainment for a sunny afternoon.

So after our previous evening at the Madison Beach Hotel, with a crow’s nest view of the Long Island Sound,

Room with a (great) view Room with a (great) view

we skedaddled off to Chester, a pleasant 30-minute drive away. Once in town, we hit Simon’s Marketplace, a gourmet general store;

Simon's Marketplace Simon’s Marketplace

then, cup in hand, we strolled past Restaurant L&E (contemporary French, “excellent eel,” says the NY Times), Pattaconk 1850 Bar &Grill (upscale pub grub), and River Tavern (brick chic). Plenty of dining options—definitely not back-road cuisine.

Dining on Main Street Dining on Main Street

Ducked into a few pretty shops, but blue skies lured us on to the Chester-Hadlyme Ferry, a “historical landmark” that’s been operating for over 200 years (it was used during the American Revolution), and is definitely the most fun way to reach Gillette Castle.

See the castle in the distance? See the castle in the distance?

A budget-travel $3 ferry ride later (car rate, but rates are doubling—walkers will now pay a whole $2), with the castle looming ever nearer, we debarked the Selden III after our 5-minute boat trip and began the vertiginous ascent (there’s a driving road, too, but the climb is fun, and over quickly).

The castle is amazing. From a distance, it looks like a medieval sand castle, dribbled on top of a cliff.

Gillette Castle
Photo/Art by Annie Graves
Gillette Castle looks more like someone dribbled sand…

Up close, it’s a handmade work of art, with no uniformity, and plenty of crooked lines and unmatched stones. It jigs and jags and meanders and soars.

I could go on... I could go on…

It’s living and breathing, and speaking of breath, the views of the Connecticut River from the terrace will certainly take it away.

Nice view... Nice view…

The story of the castle is almost as good as its looks.

See the cats on top? See the cats on top?

It was designed and built by William Gillette in 1914, who portrayed Sherlock Holmes on stage for over 30 years. An inventor as well, he tinkered with the insides as much as the outsides, designing most of its contents, and taking 25 years to complete the 24-room mansion, raised from local fieldstone.

A Gaudi moment... A Gaudi moment…

With no heirs, his will stipulated that the estate could not go to a “blithering sap-head who has no conception of where he is or with what surrounded.” The state took over the property in 1943—there are hiking trails encircling the castle like webs of time.

A definite off-the-map day….

Where are we, Dorothy? Where are we, Dorothy?

Have you ever visited Gillette Castle?

Please Note: This information was accurate at the time of publication. When planning a trip, please confirm details by directly contacting any company or establishment you intend to visit.

Annie Graves


Annie Graves


Annie Graves is a regular contributor to Yankee. A New Hampshire native, she has been a writer and editor for over 25 years, while composing music and writing young adult novels. Find out more about Annie at
Updated Friday, March 18th, 2016

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4 Responses to Gillette Castle and Chester, CT

  1. Ellen June 7, 2013 at 5:59 pm #

    Living in southeastern Connecticut, my husband and I take visitors to Gillette Castle and Chester, using the ferry. We also include nearby East Haddam (home of Goodspeed) and the Essex Steam Train and Riverboat trip. It makes for a full day of adventure.

  2. Gail Beecher June 18, 2013 at 7:09 am #

    Growing up in this area I spent many hours exploring this gem. Moving about 1/2 hour away to Preston another rural area, I now own #Roseledge County Inn and Farm Shoppe, and Gillettes Castle is one of my favorite places to send guests!

  3. Shirley June 18, 2013 at 1:20 pm #

    I am always interested in knowing if these lovely areas are handicap accessible. I use a scooter to get around so can only go where that is able to maneuver. Can y ou let me know please if that is possible for the Castle tour. Thank you.

  4. Fran Fairfield June 19, 2013 at 2:19 pm #

    My father was an over night guest of Gillette’s when the constructing the rail road was taking place.

    Apparently one evening there was quite the electrical storm raging.
    Dad remarked how the lightning eliminated and danced about the room through the small windows as he and his host enjoyed after dinner drinks by that huge fireplace.

    As a child in the 50’s we visited the castle and dad showed me the guest quarters he used.

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