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Thursday, June 21, 2012

Kayaking The Thimble Islands: The Diamond Necklace of the Connecticut Coast

This week my friend Alan and I kayaked from Island Bay to the Thimble Islands in Stony Creek, Branford, Connecticut.  It was my turn to drive so I loaded my 14-foot Merlin sea kayak onto the roof rack and picked up Alan and his 18-foot sea kayak and headed down Route 17 from Middletown through Durham.  At the Route 77 interchange we turned left for the long drive through rural Durham past rolling meadows and old-time cow farms and newer single-family housing developments which have been displacing the old family farms over the past few generations.  The road took us to North Branford past the long narrow lake on the left and finally to Route 95 South which appears out of nowhere as a hulking concrete behemoth.   A few exits later we left the concrete jungle of the expressway and turned onto the access road to Stony Creek, Leetes Island Road.  We followed the twisting road past 18th century houses and marshlands.  At Shell Beach Road we turned right and reached our put-in at Shell Cove on Island Bay.

The cove is accurately named for all the remains of clam shells which are sprinkled like rock salt on the sandy shore of Long Island Sound.  A sign on a metal post advised clammers that it was safe to dig for clams at that spot on that one day.  Later in the afternoon, at the end of our trip, a man who has clammed in the area for over 30 years explained that the state environmental official who lives on the beach nearby checks the water quality each day.  If the bacterial level is too high he unlocks the lock which holds the "Safe for Clamming" sign in place, flips it over, and alerts the clammers to dig for their hors d'oeuvres at one of the other areas monitored by the state.

The little beach at the cove is covered with a mix of small rocks and clam shells.  They lie on top of and are embedded in the rich dark sandy mud at the water's edge.  We loaded our hatches with our dry bags.  In mine was the car key at the bottom, a bathing suit and towel, and a light paddling top.  I also carried an extra bottle of water in case I ran through what I carried in the water-filled Gatorade bottle which was held in place in the black elastic rope rigging in front me on the deck of the boat.  It was high tide when we pushed off from shore and the light wind was blowing from the southeast.  Since our Thimble Island destination was several miles to the southwest, the wind would be at our backs and I figured I didn't need the paddling top for the trip out to the islands.  A lightweight quick-dry tee shirt, sunglasses, a hat, and sunscreen on the exposed skin was all that was needed on this mostly-sunny day.

On the way southwest out of Shell Cove into Island Bay we passed a grandfather and grandson on the west shore operating a small red radio-controlled sailboat.  They waved to us and I waved back to acknowledge them.  We took care to stay out of the way of the little toy sailboat.

Clark Point marks the western end of Island Bay.  As we continued southwest past Clark Point, we passed Harrison Point.  The area between Clark Point and Harrison Point is a lovely little bay inlet called Little Harbor.  Continuing southwest we approached what is called Narrows Island.  Narrows Island is actually a peninsula attached by a small spit of land to the larger Leetes Island.  Like Narrows Island, Leetes Island is really a peninsula, at the southern tip of Hoadley Neck, which is part of the mainland.  Both Leetes and Narrow Islands are populated with large summer homes.

As we continued paddling southwest, the southeast wind was now blowing against the tide, which was beginning to ebb and move the Sound's waters to the east.  As we paddled past shallower waters, the action of the wind against the tidal current created some large standing waves which required us to pay careful attention to our balance to avoid our kayaks tipping over.  Alan and I are seasoned Eskimo rollers, especially in our smaller surf kayaks, but the water was about 64 degrees and we were not particularly interested in getting wet and having our upper bodies chilled by the wind as we continued paddling.  Being early in the season, neither of us has spent time practicing our Eskimo rolls, so we carefully braced our boats with our paddles as we paddled through the shallow, wave-filled areas.

The Thimble Islands are a collection of several hundred islands, large rocks, and sandbars.  The smaller ones are only seen at low tide.  Less than two dozen have houses on them.  The islands are pink granite outcroppings left over from the Ice Age.  The Thimbles look a lot like the pink granite islands off the cost of Maine.  The nice thing for lower New Englanders like us is the close proximity of The Thimbles to anywhere in Connecticut.  It would take hours to reach the coast of Maine, but the Thimbles are just 45 minutes away from Middletown.

As we approached the Thimble chain, we took refuge in the lee of Helen Island, to get some relief from the southeast wind which was gaining velocity as the day progressed.  After a short rest to get a drink of water, we paddled southwest between Money Island and the much smaller East Stopping Bush Island.  Money Island is the most populated of all the Thimbles, with several dozen houses largely concealed among pine trees and oak trees.  We were paddling during the week and it was still early in the season, so most of the homes seemed to be empty of their owners.

Our ultimate goal was the last island in the Thimble chain, Outer Island, about 4 miles from where we started.  On our way to Outer Island, we passed between Horse Island and a tiny island which has a one-room house on stilts on it.  The little island with the stilted house is so low that storm-tossed seas occasionally cover the rocky prominence completely.  Without the stilts, the tiny house would be completely flooded with sea water during those bad weather conditions.  Horse Island is shaped like a horseshoe.  On the south side of the island there is a little cove where I've gone ashore up to the mean high water mark to eat lunch or take a swim.  Yale University's Peabody Museum of Natural History owns Horse Island and maintains an old victorian home well-hidden by tall trees.  The university uses the island for ecological research.  Alan and I decided to paddle on to Outer Island.

Outer Island and Horse Island are a few hundred feet apart.  In the channel between them, the ebbing tidal current was gaining strength by the time we reached this point.  The wind swell and tidal rip currents were pushing our kayaks towards the northeast so we had to paddle a bit harder to gain entrance into the calm water of the harbor between the rock jetties of Outer Island.  We landed our kayaks, got out, and were greeted by two young women who live as caretakers on the island.  The women offered to give us a tour, which was a kind offer, but Alan and I were quite familiar with the island from prior trips, so we declined.

Outer Island is smaller than its neighbor, Horse Island.  Outer was once owned by Yale Professor Hird and his wife.  They lived in the wood framed house nestled back in the thick grove of trees on the south side of the island.  After the death of her husband, Mrs. Hird gave the island in the 1990's to the National Fish and Wildlife Service for preservation, upkeep, and public access.  Pictures of Mr. and Mrs. Hird, and the story of their ownership of the island are preserved in a permanent color plaque next to the little harbor and sandy beach where we landed.  Alan told me he had been part of the Connyak (Connecticut Sea Kayak Club) group which participated in the ceremony surrounding Mrs. Hird's giving the island to the federal government.  Connyak now helps to maintain the island and one of its members, Bill Anthony, built a wooden outdoor roof structure next to the little barn between the beach and the house.  The handsome addition of the roof structure has a picnic table underneath and is the scene of talks and presentations about the history and ecology of the Thimble Islands and Long Island Sound.

After leaving Outer Island, we paddled around the west side of Outer Island, then between Pot Island and High Island, both of which have houses on them, finally heading to Governors Island.  Governors Island is L-shaped and has many houses, one of which is a large home nestled back in the trees which is owned by the cartoonist Gary Trudeau and the TV journalist Jane Pauley.  We then paddled east past Flying Point, at the south end of Thimble Island Road, which runs through the borough of Stony Creek and contains the mainland which looks out to the southwest over the entire Thimble Island chain.

Before paddling back into Island Bay and our original starting point, we paddled another 2 1/2 miles from Flying Point over to Sachems Head Point in Guilford.  This was good practice for the 2-mile open water crossings I like to do between Nappatree Point, Rhode Island and the east end of Fishers Island, New York.  The southeast wind was picking up and we were now heading directly into the wind, so we stopped at a rock outcropping so Alan could use the "natural facilities" and I could put on a light paddling top to stay warm.  After exploring the western part of Sachem Head Point, its harbor, and yacht club, we paddled another mile-and-a-half back to where we began the day at Shell Cove, passing Joshua Cove, between Island Bay and Sachem Head, along the way.

The Thimble Islands are the diamond necklace of the Connecticut coast.


  1. Sounds like a great paddle, Bob. I remember when you and I paddled in that area (I think) several years ago.

  2. Great travelogue; another example of your ability to bring the outdoors to life through the written word. An almost "Jack Londonish" account of the wild right here on our Connecticut shore. Keep up the good work. (One small correction so that your collective printed journal will be more accurate; it is hors d'oeuvres, but that small typo on your part does nothing to detract from your visual story.) You are a skillful writer who obviously enjoys life and the outdoors. Tres desciptif prose! You have much to offer your true followers and friends with your written account of life's adventures.

  3. I'm supposed to believe that there is a Pot Island next to a High Island? Please put up a picture of map.

    1. Dear Anonymous (June 24, 2012 at 7:35 p.m.),

      Here are links to a nautical chart and a satellite photo of the Thimble Islands. These show Pot Island and High Island and the channel between them.

      The nautical chart is here:

      The satellite photo is here:

      All best,


  4. Necklace of Connecticut……I like the sound of that. Sounds like an awesome adventure.
    Once I had read about someone secretly buying up a bunch of those islands not long ago.
    You ever hear that story? I never did find out who or why. Perhaps you should research.
    Maybe some of your readers have heard or they’d be interested in the story just the same.
    Connyak is not a group I heard of before. Have they been around long? Do you belong?
    Also, I heard some of those islands are large with many houses, others just big enough to
    fit maybe one or less. And the price of them….wow…like millions of dollars. I wouldn’t
    own if I could. I mean you spend all that money for an island that to get to you need to
    row out to every time. Not my idea of a luxurious vacation spot. But who knows right?
    You should try to get a rental I out there and spend some time……I bet the area would
    offer the inspiration for your writing; the calm, quite, scenic beauty. Everyday you wake
    up you have that going for you.

    1. Dear Anonymous (June 26, 2012 at 7:55 a.m.),

      The story about the buying up of a number of the Thimble Islands is well-summarized in this excerpt from the Wikipedia entry on the Thimbles: "In 1976, party goods magnate John Svenningsen of Amscan, Inc. purchased West Crib Island. After his death in 1997, his widow Christine Svenningsen purchased Wheeler Island in 1998; followed by Rogers (also known as Phelps), Jepson, and Cut in Two East in 2003; Reel in 2004; Cut in Two West in 2005; Beldens in 2006; and East Crib in 2007—at a total cost of more than $36 million, thus making her the largest residential taxpayer in Branford. She has also come under some criticism by neighbors of her mainland house, who have complained about trucks going in and out as renovations are conducted on her islands."

      Rogers Island is one of the larger Thimbles and contains Christine Svenningsen's large brick mansion with pool and formal gardens and a gray colonial home which functions as a guest house. The island is dense with foliage and trees and contains beautifully landscaped formal gardens. A number of years ago I was finishing kayaking the Thimbles and was paddling back to Stony Creek harbor where my car was parked. I passed by the east side of Rogers Island and sat in my kayak as I counted 24 landscapers and domestic workers come out of the wooded area near the long dock to be ferried back to the mainland. It was clear from this assembling throng that whoever lived on the island had a lot of money to be able to pay for this large a work force.

      As for owners of the houses getting to and from them from the mainland, there is a charter water taxi service which runs among all the island in the summer. The people who can afford to own a Thimble Island house either take the water taxi or own their own boats for water transportation.

      Connyak, the Connecticut sea kayak group, has existed since at least the 1990's. I don't know the exact year of its founding. The group offers instruction to beginning sea kayakers on an informal basis and organizes sea kayak group paddles throughout the summer months.

      Thanks for writing your Comment.

      All best,


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  6. How you doing these days, man? No posts since June. Hope you're okay. Can you share an update?