Thimble Island's Boat Tour

The Thimble Islands are an archipelago of more than a hundred islands (depending on the tides), just off the coast of Stony Creek, CT. The Thimble Islands are mostly privately owned and contain some truly spectacular real estate.

My parents and I decided to take a boat ride around the islands. Our captain for the day Captain Dave Kusterer's and his 26-foot port launch, The Islander, carries eighteen passengers on a roughly 45 minute tour. Our tour lasted about 50 minutes. Captain Dave prefers to use a smaller boat since he says it can reach many areas of the Thimble Islands that cannot be accessed by larger vessels. The Islander can only take 14 passengers at a time for both safety and to provide a comfortable less crowded cruise for all its passengers.

After a brief safety speech we began our voyage around the islands. He starts off with a quick listing of the statistics of the Thimble Islands. We learn that there are 365 charted rocks and islands contained in the 5sq miles known as the Thimbles. 21 of those islands are inhabited and have a total of 95 homes built. 120 families share these homes but only 2 people live here in the winter.

Known only to the Indians until discovered in 1614 by Dutch explorer Adrien Block while mapping the CT Shoreline. They first appeared in British Nautical chart in 1701 and they were called the Hundred Islands. 33 years after that they were renamed the Thimble Islands after the wild berries that grew all over them. Those thimble berries are known today as the common raspberry.

The first island we approached is called Wheeler Island. It’s so close to the shore during low tide you can wade through the waist high waters to it. Today is has been redone top to bottom. The old house on Wheeler Island was in such disrepair when purchased that the new owner had an exact copy built in its place. It’s called the Old New House. It has never been lived in since being redone 10 years ago. The rumor is that the new owner a wealth widow has been slowly purchasing up the islands as gifts to her children. When they are old enough she will hands them each a key to their very own island. She currently owns 10 of the major islands.

The original owner of Wheeler Island was Captain Frank Wheeler. As history goes the house was so run down that the kids on the main land thought it was haunted. He would wear all black and walk around the house with just a single lantern playing his violin which were heard by kids and thought he was a ghost. This act was witnessed by Charles Adams’s of the New Yorker Magazine and was inspired by this a painted a portrait of the house that landed on the cover of the magazine just in time for Halloween.

He explained that all the stone work you see around the islands is pink granite. Stony Creek pink granite is a favorite amongst monument builders and has been used like the Grand Central Station, George Washington Bridge and the steps of the Capital Building in Washington DC.

We learned that they have a 6.25 ft tidal flow on average except during unusual events like last night’s unusually close moon that resulted in a 7.25 ft tide which left one of the three main tour boats grounded for several hours in the harbor. The tides play an important role when weather turns. During September 23, 1938 it was calm but by the end of the day two storms a hurricane and a nor’easter had converged on each other creating a perfect storm. It blew across the islands sent many of the inhabitants fleeing during high tide only to discover that it would continue to rise over 8 ft past the high tide line. During that storm 9 houses were lost along with 27 souls in the Thimble Islands.

Evidence of hurricane damage can still be seen between Cut-in-two East and Cut-in-two West which were once connected by a foot bridge. The bridge was never rebuilt because the owners at the time disliked each other. Like Wheeler Island the same wealthy owner purchased both of the Cut-In-Two islands. One of the two islands Cut-In-Two East was owned by the Warren family whose daughter Lavinia was very short in stature at 3’ tall and went to work for PT Barnum. While working for him she meet and married Tom Thumb the shortest man on earth. Rumor has it each time he and his wife would visit the island he would bring a circus poster with him and to this day one of the rooms is wallpapered with these posters. These posters are priceless and are worth more than the house and the island combined.

Only 6 of these islands have electricity (wire) and 9 have running water (hose) and most have neither. Electricity was brought to the islands in 1961 but not all islands opted into getting the offered services. Since not all islands have electricity today if an island owner decides to get it they can no longer run power in under water conduits and must go over the water. For example the new owner of Cut-In-Two East and West want electric on both islands they are reconstructing the foot bridge to bring power to the second island from the one that already has it.

Captain Dave told us that his favorite island was Dog Fish Rock at ¾ of an acre. It had both wire and hose and was just the right size. He explained that if the island is too big you are always working on it and if it’s too small you get rock fever and can’t wait to get off the island.

As our voyage continues we passed Davis Island which he described as the most luxurious of the Thimble Islands. On Davis Island is what is called the summer White House since President Taft had stayed there for a few season. It includes a man maid harbor where it keeps the boats and toys safe from the surf. Another interesting factoid about Davis Island and the Summer White House was that our captain kissed his first girl on the widow’s walk of the house. It also has solar panels that not only cover their electric needs but pays them back.

Someday Island was a lesson in not waiting. During the ’38 hurricane the house that was there was unceremoniously washed off the island. It got the name Someday because the owners talked about someday rebuilding. It never happen and now with the rules having changed in 1973 they can no longer build since they do not meet the requirements for septic systems. They sold it for what they could get and the new owner built a dock and nothing more. The dock was washed away during hurricane Irene and it was never rebuilt.

Money Island is the most popular island and had many community amenities like a general store, a chapel, post office and even at one time a bowling alley. Many of those buildings were turned into more summer homes or just simply torn down. Currently there are 21 homes on Money Island. The biggest threat to the island is fire and the community spirit is alive and well and they are all part of the bucket brigade.

Money Island is also one of the supposed places that Captain Kidd buried treasure. Having lived on the island our Captain has never found any of the suspected treasure. Our Captain who grew up on the island has himself searched and found nothing but poison ivy.

Greyrock is another of the many islands. The house was built from 1900-1910 and built the house foundation from rock quarried from the island and the lumber brought out on a barge. They even used the wood from the barge for the heavy timbers as the framing of the house.

Mother-In-Law’s Island is another small island with a fun story. As rumor has it a couple decided to honeymoon camp site. The first night the mother of the bride showed up in a rowboat. When mom didn’t leave and fell asleep on the island the newlyweds left and took her boat with them leaving her stranded. She tried to capture the attention of people on Money Island they brought her food but left her. This is how it got its name.

All the islands where formed or reshaped by the glaciers. Glaciers left potholes that would trap water when the tides went out and the Indians used the islands as campsite and bathed their children in these potholes. Pot Island where many of these pot holes were found. In 1846 a hotel was built here. It was after the completion of the hotel that the new owner renamed it Treasure Island to draw more attention to it.  It was a very popular place until the depression hit and it never recovered.

There are no hotels any longer because of the clean water act of 1973. Septic system are a problem and light use is the only thing that keeps them alive.

One of the smallest islands is called Exton’s Reef Island. The house is built up on pilings leaving much of the island underwater. It has no grown and as a result no septic but because it was built before 1973 he is grandfathered in.

The next island is called Horse Island and it was here our Captain worked as a kid clearing debris for an upcoming wedding. He was to be paid at the end of the summer but when the wedding day arrived the groom’s wife wouldn’t let him come as it turns out he was already married. The bride and her family were so upset they tossed all the silverware in the ocean. He never got paid since they left the following day and never returned. He dived for the silverware but as it turns out it wasn’t the treasure he hoped since it was all silver plated. Today its owned by Yale University for research.

The furthest island out is called Outer Island. It’s a public island and is only accessible by boat and many people kayak out or take one of the ferries. There is no camping or glass allowed on the island. It allows you to be an islander for the day for free.

We learned that our Captain was born on the next island called High Island. His family was tasked with opening up the house and they didn’t make it off the island before his mom gave birth. It’s the tallest island of them all and was a rumored hide out of Captain Kidd. People say he buried treasure here but he wasn’t a pirate he was a bounty hunter. His crew went after three cargo vessels flying the French flag but actually owned by the British East India Company.

When the crew discovered this they over powered their captain and took the bounty. Accused of being a pirate he his out in the Thimble islands while he tried to sort it all out and get his name cleared. We know for sure that he was here because in what’s known today as Kidd Cove because etched on a rock was the name James Dimmons’s who was a crew member on the Adventure Galley.

The island doesn’t have electricity or water. Today they use propane and collected rain water. They stored their water in cisterns. The cistern’s provided both water for living but also as water to battle fires.

Taxes are a big problem and a source of argument. 2 million in taxes are collected but only about 5000 of that is used for trash collection. Other than that there are no town services on the islands. Governor’s Island was the most popular location for the Indians’ because of the shallow waters around them. Made collecting clams and casting nets easier. Most of the island’s homes were built by the 1930’s. it is the 2nd most populated island. What makes it special is the 40 different trees found here all planted by Charles Weed. It was his hobby to see what would grow.

In 1901 one visitor decided he wanted an island of his own but none were available. He bought a rocky out cropping and made and island of his own. Today it’s called Potato Island. The island got its name because the 5 rocky out cropping’s were called the five potato’s. He used them as a foundations and built a sea wall which he filled inside with soil and built two homes. In 1938 one of the two homes was wiped out. The last remaining home was repaired. Today it has a swimming pool where the old house stood.

The biggest island is Roger’s Island at 11.2 acres. Its history started as a granite quarry. The stone taken from the island is the base of the Statue of Liberty. It was sold to Captain John Kelps. He built a Tudor mansion. His was involved in copper mining. After his death his daughter inherited the island in 1936 but didn’t want it. She once said if she knew how much to sell it she would. A guy named McCloud helped her figure out its value sight unseen and concluded it was worth $56k. He purchased it having never seen it he was surprised to find the house and the inside filled with valuable antiques and paintings. He sold them off recouping his initial investment and then sold the island 6 months later for $1.2 million.

Today it’s the home of the widow who has been buying up the other islands for her children. She paid 22.3 million to purchase it. It is currently covered in palm trees that in the winter are put in their private green house. She spends 2-3 weeks a summer on the island and has over 31million invested in the Thimble Islands.

They also own Belden Island where they are currently filming “the Love Prison” where people who meet on the internet are put on the island to see how they get along. Its scheduled to be on A&E in the fall.

Currently there is 1 island for sale. It’s called Cedar Island. It can’t be built on but it has a small gazebo and is used as a backyard. Those that visit can sleep on a boat docked nearby. Its currently listed for $285k. The next cheapest island is over $2million.

With that we finished our loop through the islands and headed back to dock. We had a great time and learned a great deal about the Thimble Islands.