More than 1000 gems in the 1000 Islands

The Thousand Islands are a group of more than 1,800 islands in the St. Lawrence River, straddling the border of the U.S. and Canada. A fashionable retreat for the elite in the late 19th century when folks arrived by railway or steamship, the area is busy these days with boaters galore – large, small, beautiful old wooden boats, trawlers, sailboats, noisy “cigarette” boats, tour boats, ferries, and large freighters. Some islands are literally a bunch of rocks with one tree, just big enough to house a small house or host a flock of cormorants, and others are larger with communities, farms, houses, and recreational parks. Each one has its own characteristics and personality.

American 1000 Islands Bridge

The 1000 Islands are divided by the US/Canadian border with a 1000 Islands Bridge connecting us.

We greatly enjoyed exploring the islands over these two weeks (July 2019) on both the American and the Canadian sides. We had to clear customs when entering Canada to either anchor or dock, and the restrictions are complex. We have to go to a port or town that has a customs reporting mobile phone station, and Dean, as our captain, has to share details of our travels, our ship’s supplies, and our passport information. Once “approved,” we get a formal entry # that we have to display on our boat and we raise a Canadian courtesy flag. We chose to enter Canada at the port of Rockport, which is a small town with a bustling tourist business – tour buses come in so folks can take a ferry or tour boat to cruise the 1000 Islands and visit the beautiful and majestic Boldt castle. More on the castle later.

Andress Boat Works shop
Rockland 🇨🇦

We opted to stay in Rockport 🇨🇦 for the afternoon so we could bike on the St. Lawrence Seaway trail. We always try to take an opportunity to hike, walk, kayak, or bike ride when we can – living on 36’ limits our physical activity. The bike trail is a 330km (205 mi) trail from Kingston Ontario to Montreal. We rode ~ 15 miles from the coastal town of Rockport to a larger town of Gananoque. Lovely paved path with rolling hills and minimal traffic, and glimpses of the Canadian 1000 Island Bridge and the SL River. Significant headwind biking over gave us a good workout, while the return trip felt like an easy “spinnaker run.” We visited the marina in Gananoque and retrieved a lovely “welcome” bag from the local AGLCA (America’s Great Loop Cruisers Association) Harbor Host, Jim Lund, with lots of helpful local information. We were scoping out the town as a potential place to take our 1000 Island leg guests, Dean’s brother John and his wife Cindy. Especially if the predicted wet weather dominated our week.

Biking! In Canada!

One of the larger 1000 Islands, Grindstone, was worth several visits. Grindstone Island is the fourth largest of the Thousand Islands in the St. Lawrence River and the second largest of the American islands in the St. Lawrence. We first anchored off of Picnic Point, a scenic point famous for fishing camps and the origin of Thousands Island dressing, which local lore says that a fishing guide’s wife, Sophia LaLonde, made the condiment as part of her husband George’s shore dinner. Guided fishing trips and fishing camp dinners were big business in the early 1900s in this region. There is still a reserved pavilion for fishing guide dinners.

Picnic Point

Picnic Point offered loons and babies, swans and baby cygnets, squawking herons, and beautiful trails through the island, along with kayaking and swimming. It is a very popular anchorage on weekends especially with day boaters.

Laughing loons all night
Swans are so protective of their young
We passed a large heron rookery on Yeo Island,
with more than 50 nests easily seen
Anchoring was tricky with all the marsh grass but…
(our friend Steve’s Monk)
…well worth the effort to anchor in this beautiful place
📷 credit Steve Dettman

Grindstone has ~ 400 summer residents and < 10 winter over we hear. There are mostly trails on the island, and most residents travel via ATVs. There is an active Methodist Church on the island that draws a crowd for Sunday services from all around. Grass Point, close to Picnic Point is a NY state park for camping with an attached state marina. It was a busy place, with lovely grounds, and connected to the trails as well.

Best find on the island for us was the Grindstone Island Winery, a 2.75 mile scenic walk through the island trails. They do plant a few bikes on the trail that people can borrow and ride to/from the winery, but we opted to walk despite the hot, hot day.

Julie Tinney is a one woman business, from planting and growing the grapes, to making the wine and bottling, to running the wine tasting and sales from their beautiful building, complete with red granite counters quarried from the island. She was so knowledgeable about island life and wine, and was wonderful to listen to. She set me up with a cold refreshing root beer slushee (and I chatted with other boat travelers), while Dean, John, and Cindy had an extensive wine tasting experience. So many corks…

Highly recommend a visit!
The 2.75 mile hike back to the boat was…necessary

I love reading about the areas we are discovering, beyond the cruising guides and charts. There have been two books we’ve read on the culture, people, history, and geography of these amazing islands. GRINDSTONE: An Island World Remembered, by Stanley Norcom, is an excellent and well written memoir of a summer life on Grindstone and the people and places for almost a century of the author’s life. A wonderful peak into island life in the 1900s.

A beautiful photo art book also has wonderful photographs and brief information about many of the islands. The 1000 Islands: The Photography of Ian Coristine is a coffee table type book with nuggets of info included.

River life revolves around boats, especially for transportation including travel to and from the many island homes. Most houses have a boat house, and this year many are riding low in the water with docks covered. But, like the islands, the boat houses are variable and have a personality of there own.

Notice the blue barrels, holding the docks that are submerged

We’ve been in and out of Clayton NY a few times, docking at the Clayton Village Municipal Dock on Mary Street, next to the Antique Boat Museum. Simple dockage with electric, water, showers, laundry and friendly dock staff, but best of all is the close downtown location. Clayton was once the hub for access to the islands as the railway came here from NYC and the elite began summering on the islands from here. It has a lovely walkable town with shops and restaurants on the river, and Dean was able to find an old fashioned barber for a trim. We picked up our current crew, John and Cindy, here and were able to store their car for a week easily in the public lots. A fun town to explore and to restock the boat – the local Shurfine supermarket even will pick you up and deliver you back to the boat after shopping!

The Antique Boat Museum is a wonderful way to spend a bunch of hours – time well spent. They have a campus with several building with different themes (“Quest for Speed”) along with boat building shops, sleek wooden boats in their boat house, antique motors, and the opportunity to tour the 106’ houseboat La Duchesse, built in 1903 for hotelier George Boldt of the Boldt caste and Waldorf-Astoria fame. A classic beauty.

Classic wooden beauty – love the owl bow lights
My dad loved working on wooden boats for years so I appreciate the workmanship
graceful lines

Boldt castle was another worthwhile stop and it was a great to be able to access it from our boat, rather than having to join a large commercial tour boat excursion. However, because of the low docks/high water issue, we did have to anchor in the bay between the castle and the yacht house, and dinghied in to the landing. We went on a weekday, so it wasn’t overly crowded.

The main castle building

The history of Boldt castle is fascinating and considered a tragic love story. George Boldt, a hotelier famous for his management techniques of the Waldorf-Astoria and Bellevue hotels, built the castle and other island structures as a birthday/Valentine’s gift to his wife, Louise. Located on the island of Hart, which Boldt renamed Heart and modified the island shape to resemble a heart, construction began in 1900. Before completion, Louise Boldt died unexpectedly (and mysteriously, we heard) and George Boldt ordered workers to stop construction immediately, and the massive project was abandoned. A broken-hearted George Boldt reportedly never set foot on the island again and the castle sat to decay for over 70 years, until the Thousand Islands Bridge Authority began renovations in 1977. The opulence of the castle, the out buildings, and the grounds are stunning.

The first level of the Playhouse, which looked like a sandcastle,
housed the pool, billiards, and a bowling alley.
The Power House with the Clock Tower,
designed in the fashion of a Medieval Tower. 
Mrs.. Louise Boldt on her wedding day
One of the many unfinished passageways
One of the Italian garden sculptures.
Many details of the gardens, frameworks, and ceramic moldings
were heart-shaped like this garden

Many more wonderful things to share about the 1000 Islands but this account is long enough. We will find more wonderful anchorages with John and Cindy, before heading back to Clayton NY one more time for some boat repairs. Then off to Kingston ON 🇨🇦 and a start up the Rideau Canal toward Montreal.

Where in the northeast US is trawler Clare? You can find our latest location always here.

By the grace of God we go,

~ Karen and Dean

Goodnight, from the Summerland islands anchorage

Categories: Canada, July2019, New YorkTags: , , , , , , ,


  1. Oh Karen and Dean! Looks like an amazing journey!! Love reading your posts ~ I wanna come!!! Hugs to you both and John And Cindy!

    😊 Ellen & Steve



  2. What beautiful memories you’re making!


  3. Such a wonderful trip you guys are having! Thanks for taking us along with you.


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