From our vantage point in the cockpit of our sightseeing helicopter, it was easy to see why Gananoque, Ontario is known as the Gateway to the Thousand Islands. Stretched out below us along the St. Lawrence River was an archipelago of islands, some barely larger than a Toronto front yard, some large enough to be home to fairytale castles. With the fall colours painting the tops of the trees in shades of amber and red and the transparent blues of the water looking almost tropical, I couldn’t think of a better way to take in all the beauty of this Ontario region than from the air.

Our flight was undoubtedly the highlight of our grownup getaway to the 1000 Islands Gananoque region, but even on the ground – or on the water – there was much to see and do here that impressed us, and of course, everything came with a story.

But First, Let’s Talk Islands!

The 1000 Islands region near Gananoque, Ontario is home to many more than the thousand islands after which it is named. There are actually 1,864 islands that make up this region, each one of which must meet proper ‘island’ criteria in order to be counted: meaning the land must stay above water all year long and support at least one living tree.

Some of these islands are privately owned with beautiful turn-of-the-century cottages, some are uninhabited and home to unique ecosystems, and others support the foundations of the 13.7 km-long Thousand Islands International bridge that links the United States and Canada.

Not surprisingly, there are almost as many stories as there are islands when it comes to the Thousand Islands’ local lore. These islands have inspired tales of shipwrecks and smugglers, pirates and buried treasure, celebrity sightings and even secret societies (the Skull and Bones Society of Yale University has property on an island here). Of course there are also stories of romance…

Boldt Castle: A Romance that Ended in Ruins

One of the most romantic stories told in the Thousand Islands involves Boldt Castle, the extravagant 120-room European style castle that American hotel magnate George Boldt envisioned as a gift for his wife, Louise. Boldt knew of the 1000 Islands region from vacationing here with his family, and he decided to purchase a small island on the American side of the St. Lawrence near Alexandria Bay called Hart Island where he would build this dream home. A hopeless romantic, one of the first things he did was construct breakwaters around one end of the island to alter the shape of the island just enough to create a more heart-shaped perimeter and justify his renaming the island Heart Island.

Boldt had made millions as the man behind the luxurious Waldorf Astoria hotel in New York City, the first hotel to cater to the uber-wealthy and to make staying at the hotel not only fashionable but a status symbol. Boldt applied these same high standards to the summer home he was building, bringing in skilled artisans and expensive materials to create what looked like a European castle, complete with towers, underground tunnels, turrets and formal gardens.

No expense was spared in the design or the details, and although historically-inspired in its architecture, the Castle was outfitted with all of the most modern amenities of the day. The Power House and Clock Tower right at water level may look purely decorative and fanciful, but this structure actually housed a sophisticated steam generator system used to power the whole island.

The forbidding-looking Alster Tower was actually designed as the ultimate games room of its time, and included a two-lane bowling alley, kitchen, billiard room, library and theatre. For children, it was a dream-come-true Playhouse (which became its nickname), and for adults, a fanciful entertaining space.

Sadly, like many a great romance novel, the story of Boldt Castle ended in tragedy: Louise Boldt who had been ‘in delicate health’ for some time, died suddenly before the castle was completed. George was so devastated by her death that he ordered an immediate halt to the construction, and never set foot on Heart Island again. The Castle was abandoned and left incomplete for more than seven decades, ravaged by weather and vandals until 1977 when the American Thousand Islands Bridge Authority acquired the property and began restoring the property both inside and out.

Visiting Boldt Castle Today

Today Boldt Castle is one of the most visited destinations in the Thousand Islands Gananoque area, attracting more than 200,000 people annually from Canada, the U.S. and the world. And the best way to see it is actually from the water on a guided boat cruise, several of which leave from Rockport, Ontario just outside of the town of Gananoque.

Henk and I took a 1-hour Heart of the 1000 Islands cruise with Rockport Cruises, which gave us a close-up tour around the island as part of our route. Rockport also has longer boat tours including ones that offer visitors the chance to land on Heart island and spend time touring the interior and exterior of the Castle and the grounds. Unfortunately we weren’t able to do this because these excursions had been put on hold due to border crossing complications due to Covid. The good news is, it looks like these cruises will resume in 2023!

TIP: There is also another beautiful castle in the 1000 Islands region called Singer Castle, built by the president of the Singer Sewing Machine Company, that you can visit along with Boldt Castle on Rockport’s 2-Castle Cruise. Check the cruise website for when these tours will operate in 2023, and remember to bring your passport as both of these castles are on the U.S. side of the river!

The Story (ies?) Behind Thousand Island Dressing

Boldt may have left it to others to complete his castle after his death, but he was instrumental in creating another lasting legacy from his time in the 1000 Islands: the famous salad dressing of the same name.

According to one account, while on a cruise on his yacht in the 1000 Islands, Boldt asked his onboard chef to create a salad dressing inspired by the islands, and the chef got creative with what he had in the galley: to a hard-boiled egg he added relish (for the green of the islands), ketchup (for the spectacular red sunsets) and a dash of mayonnaise (for the whitecaps on the water). Boldt was impressed and loved the dressing so much that he put it on his menu at the Waldorf and the rest is salad history.

Well, that’s one story anyways.

Another story links the dressing to a local fishing guide named George LaLonde Jr. and his wife Sophie, who would serve this dressing to their fishing clients as part of what they called their ‘shore dinners’ after a successful day on the water. The wife of one of these guests, a New York City stage actress and renowned cook named May Irwin, loved the dressing recipe so much that she asked Sophie for the recipe to take back with her to New York. There, Irwin shared the recipe for what she referred to as ‘Thousand Island Dressing’ with George Boldt, whom she knew was a fellow Thousand Island vacationer.

Boldt was equally impressed with the flavour and gave the recipe to his Waldorf Astoria hotel chef Oscar Tschirky to add to the hotel’s menu. From there, thanks to the reputation and prestige of the hotel, Thousand Island Dressing was introduced to the world.

Stories From the Past: the 1000 Islands History Museum

Small, regional museums are often some of the most interesting ones to visit because of their hyper-local collections that bring the town and region’s history to life with not just historic artifacts but the stories that accompany them. Gananoque’s 1000 Islands History Museum on Water Street is a great example of this.

The museum’s permanent collection includes several military items that highlight the role that Gananoque played in the War of 1812. Being on the St. Lawrence, the town was a critical supply location to ship goods between Montreal and Kingston and as such was a prime military target. This culminated in September of 1812 when Gananoque – literally caught in the middle between the American forces and British – was raided by the Americans who wanted the arms and ammunition that were stored in town. In the grand scheme of the war, this raid was really only a skirmish, but it still left the British with 8 wounded men, 8 men captured as prisoners of war and more soldiers and citizens wounded, including Abigail Stone, the wife of Gananoque’s founder, Colonel Joel Stone.

Aside from the military items, my favourite pieces in the Gananoque museum were photos and items that showcased the Golden Age of the 1000 Islands region from the late 19th and early 20th centuries, when people travelled from both the US and Canada by rail and ship to holiday in this area. It seemed like a very civilized and fashionable time to be a cottager, even if you didn’t have the wealth of the Boldts or the Singers.

Stories on Stage: The Thousand Islands Playhouse

The story of the Thousand Islands Playhouse began in 1982 when a group of community members purchased the historic Gananoque Canoe Club building from the local Rotary Club with the idea of converting the property into a 360-seat theatre. What started small with just 3 shows and around 6,000 patrons has since grown into one of Ontario’s top 5 summer theatre festivals with more than 40,000 annual theatre-goers.

Today no visit to Gananoque would be complete without taking in a performance at this intimate and charming theatre right on the banks of the St. Lawrence River. The stories that play out on stage here bring together talented actors and professionals from across Canada, with 80% of the productions being written by Canadians. Henk and I were treated to Tony-award winning musical The Jersey Boys, which was top-notch and thoroughly entertaining.

TIP: The Thousand Island Playhouse 2023 season has just been announced and offers something for everyone, from world-class musicals to award-winning dramas, and all with prices that make it affordable for all.

Stories in the Air: Thousand Islands Helicopter Tours

Henk and I ended our 1000 Islands Gananoque getaway on a high note – quite literally – with Thousand Islands Helicopter Tours and their must-do sightseeing flight over the area. Helicopter flights just never get old, even for Bill Fox our pilot, who has been flying choppers for years here and showing people the beauty of the region that you can only appreciate from a birds-eye perspective. And since Thousand Islands Helicopters operates all year round, Fox has seen the region at its most photogenic in every season.

Our flight day was a perfect autumn one with crisp, clear skies and wall-to-wall sunshine reflecting off the crystalline waters of the St. Lawrence. During our 20 minute flight, Bill pointed out major landmarks like the Thousand Islands Bridge, Alexandria Bay (the location of Boldt Castle on Heart Island), and the Landon Bay viewpoint near the Thousand Islands Parkway, where Henk and I had just hiked that morning.

But it was when we had landed and were chatting with Dave Kouri, the founder and President of Kouri’s Kopters, that we heard a few stories about some of the company’s more famous clients, one of them being country superstar Carrie Underwood. I had actually noticed a photo of Underwood and her then-fiancé Canadian NHL player Mike Fisher in the waiting room before our flight, so when I asked about it, Kouri told me that as a 30th birthday present for Fisher, Carrie had taken him for a helicopter tour.

I asked Dave if he had been nervous flying such a well-known celebrity, and he actually confessed that he was more nervous 3 years later when he had to fly another ‘passenger’ in 2013: the Stanley Cup!

To Canadian hockey fans, there is no bigger name than ‘Lord Stanley’, so when Kouri was asked to take Stanley Cup Champion Andrew Shaw for a helicopter tour along with the Cup, he couldn’t say no. Shaw, who hails from nearby Belleville, had won the Cup that year with the Chicago Blackhawks, earning him the right to take the Cup wherever he chose for a day. But Shaw still had to clear the flight with the Stanley Cup’s official handler, who agreed to the helicopter tour providing the seat belt could be secured around the trophy. It was a tight squeeze for a moment or two with the belt initially looking like it was about 6 inches shy of the task, but Kouri pushed and prodded on the seats until Lord Stanley was strapped in safely. Cup, Champion and Kouri took to the skies, and the rest is Thousand Islands Helicopter history.

Make Your Own Story

Gananoque may be small but that’s part of its charm, and it makes it that much easier to explore, meet some of the local shopkeepers, enjoy a drink or a meal at one of the town’s restaurants, and in doing so maybe make your own story or two (Instagram stories included).

Here are more ways to get to know Gananoque:

Explore Gananoque’s Downtown

Start with one of several walking trails that you can follow if you like a more structured route, or you can just wing it like Henk and I did and explore the downtown on your own with the help of a great new digital app that highlights historic buildings and tells their stories. (It even has a photo slider feature that shows you then-and-now photos of the specific building or location. It’s a great way to see Gananoque’s past and present at the same time.)

One of the first things we discovered was the pretty Confederation Park right on the banks of the Gananoque River. The Park is a peaceful centrepiece to the town and is home to Canada’s largest outdoor contemporary art exhibit, a collection that was started with pieces leased from the Art Bank in Ottawa.

Today the town is focused on more local artists and representing the history and environment of the area, so they have been gradually replacing the leased artwork with works by artists such as Bruce Mellon from Wolfe Island (one of the largest islands in the region).

There’s also less formal art around downtown, including barrel/planters painted with whimsical designs.

And there is always a mural or two worth capturing, even in the smallest of towns.

TIP: If you want advice on what to see and do in and around town, drop into the Gananoque’s Visitor Centre on King Street, as the staff here know their town best and can always offer up more local recommendations.

Admire Gananoque’s Homes

I love walking around residential areas admiring some of the historic buildings and homes (particularly Victorian ones), and Gananoque in the fall is one of the best times to do this. Some of the larger homes now function as B&Bs or private apartments, and with the fall colours at their peak, they were framed beautifully by the town’s mature trees.

Take a Short Hike on a 40-km Long Parkway

If you want to combine a short drive to see the fall colours with a short hike to an overlook, head to the Thousand Islands Parkway just outside of Gananoque. It’s a beautiful drive at any time of the year, but particularly in the autumn with colourful trees lining one side of the highway and the St. Lawrence River flowing beside the other. The Parkway also passes right by the Thousand Islands National Park where Henk and I did a short hike to a rocky overlook at Landon Bay.

This is one of the highest points in a relatively flat area so it does give you one of the nicest views. And the hike itself wasn’t strenuous or particularly steep, just a beautiful walk through a forest on a well-maintained trail.

A Grownup Getaway to Gananoque, Ontario

Small town getaways are some of the best ways to explore your own backyard and our Gananoque visit had all the ingredients for the perfect grownup getaway: a little culture, a little adventure, a little eye candy, and of course an interesting story or two that we uncovered during our visit.

We’re sure if you visit this charming Ontario town, you’ll have a few stories to bring back with you, too.

Special thanks to 1000 Islands Tourism who hosted Henk and I on our grownup getaway to Gananoque!

Practical Information for a 1000 Islands Gananoque Getaway

WHERE TO STAY IN GANANOQUE

Two of the most popular places to stay in town are also some of the prettiest buildings we saw, too: the Woodview Inn and Pangea House B&B. Both were recommended to us by locals, and both are on our list for our next visit. Definitely check them out if you love staying in historic buildings and small inns with charm and architectural details.

WHERE TO SHOP IN GANANOQUE

Downtown Gananoque offers several unique boutiques worth checking out, including a new and used bookstore called Beggar’s Banquet Books. It took me all of 10 minutes to find something interesting here, but I easily could have spent an hour poking around their shelves.

For clothing, there’s Drawing Room Vintage, run by an ex-pat Torontonian who made the move to Gananoque a few years ago and found a market for her vintage clothing in an historic building that is even more ‘vintage’ than the items on the racks. Connected to this shop in the same building is Steel Style Garage, which offers contemporary casual clothes for men and women.

And one of my favourite places was a home decor store called Magnolia Flowers that has a beautifully curated selection of items, and one of the most characteristic floral ‘fridges’ they designed using salvaged glass doors.

Oh, and don’t even think about trying to buy those antique bicycles on the walls…they are not for sale, we asked!

WHERE TO EAT IN GANANOQUE

Pistachio Cafe is a delightful family-run lunch spot that just opened up in 2022 offering freshly-made, casual menu items like seasonal soups, wraps, sandwiches and (delicious!) scones along with your hot or cold beverage of choice. Inside is tiny but cozy, but there’s a nice patio outside when the weather is warmer.

Laverne’s Eatery is a funky little nook of a restaurant with eclectic furniture and decor, a couple of small rooms for diners, and a menu that is largely locally-inspired. Morning menus are as fresh as their coffee, and don’t forget their tomato jam – that sweet/savoury stuff goes with everything!

Anthony’s is a family favourite in downtown Gananoque serving the kind of comfort food we all love (think hot turkey sandwiches). It’s the kind of place where you’re likely to find everyone from families with wee ones to seniors with friends. This is also the kind of place where you will find real gravy, real vegetables and real home cooking, at really reasonable prices. Come hungry.

For a more elevated dinner, head to Riva Restaurant for tasty Italian food with gourmet touches served in a beautiful, historic stone building. The atmosphere is as inviting and upscale as the menu items, so relax and settle in for a few courses and a glass or two of something sparkling by the towering fireplace.