Tiny(ish), Ontario - Kingston
- chebelladonna
- Aug 16, 2025
- 4 min read
Updated: Mar 1
Kingston, Ontario is both a central gathering point within Eastern Ontario, as well as a central character in my life. Throughout the decades I have come and gone from Kingston. We have loved, and lost, fought, broken up and always made-up. In the end, all roads have led me back to Kingston.
At 175,000 inhabitants, it is the biggest city in Eastern Ontario outside of Ottawa. While I would no longer call it tiny Ontario (as a kid Kingston was closer to 60,000), it is the regional hub. Nicknamed the Limestone City for its many limestone constructions, it lies on the shores of Lake Ontario, at the confluence of the Cataraqui and St. Lawrence Rivers. The city has a fantastic location sandwiched between the Thousand Islands to the east and Prince Edward County to the west, two beautiful areas to explore.
The city itself is historically significant. With roots back as far at the1600s, and from 1841-1844 it was named the first capital of Canada before it was permanently changed to Ottawa in 1849. (The capital city bounced around between Quebec City, Montreal and Toronto in the intervening years.) This led to a number of prominent buildings being constructed in the downtown core including a gorgeous city hall and European style market square. This is all to say that the city is a show pony. I may be biased, but Kingston can still make my heart flutter.
Kingston is known for a number things. Namely the city is rooted in military history, penitentiaries, post-secondary education, boating and subsequently tourism. Many of these roots provide the city with interesting places to visit including:
Old Fort Henry, built in the 1830s to replace an existing fort used in the War of 1812. It sits on top of a large hill on the edge of the city, and at start of the Cataraqui River. The fort was in active used until the late 1800s, and was briefly refurbished in WWI. By the 1930s it became a historic site and museum. On Friday nights in the summer they host a Sunset Ceremony where the Fort Henry Guard take to the square with impressive military displays including firing the canons. And if you happen to be in Kingston in October they run a month long event called Fort Fright. I went once; it was terrifying. https://www.forthenry.com/
Kingston Penitentiary (KP), Canada's oldest prison, was in active use from 1867 until 2013, it is often dubbed as Canada's Alcatraz. A maximum security prison, in it's early years it detained both women and children. Eventually Kingston went on to to open only one of two women's penitentiary's in Canada. During the KP's history there were three sets of riots in 1932, 1954 and 1971, the final being the most destructive. After the KP closed, it was opened to the public for tours. As someone who grew up in the area, both the KP and the Collins Bay Institutions in the heart of the city were foreboding pieces of architecture. It was eerie to step inside those notorious walls. Fun fact, six prisons remain in Kingston, even with the closure of KP and the Women's Pen. https://www.kingstonpentour.com/
1000 Island Cruising - At the head of the Thousand Islands, Kingston is a jumping off point to catch a boat tour. The 1000 Islands (actually 1864 islands), are a UNESCO heritage site and a national park. The islands are a region where the Canadian Shield meets the Adirondacks. Some of the Islands are protected within the national park, and others are privately owned and dotted with beautiful cottages. It's a stunner. 1000 Island Cruises runs a host of tours in varying lengths, and with varying interests. https://www.1000islandscruises.ca/sightseeing/
S.S.Keewatin Tour - While not specific to the history of Kingston, the S.S. Keewatin was brought to the city from Port McNicoll, Ontario in 2023. Built in 1907, it is the largest remaining Edwardian era ship, as in, a smaller version of the Titanic. The ship was built in Scotland and brought to Canada. It was even cut in two and rebuilt to get it through Lake Erie on its journey. The ship is hosted by the Great Lakes Museum and well worth the tour. Tours can be booked with the museum directly, or if you are looking for something a bit more spooky, the Ghost Walks run a haunted version of a tour, which is what we did.
https://hauntedwalk.com/experience/ghosts-of-the-ss-keewatin-tales-from-the-great-lakes/
Beyond the main tours listed above, much of the charm of Kingston lies in the simplicity of meandering the city. The City Hall gifts the city with beautiful limestone architecture, and it's well worth some time to walk the Sydenham Ward district of the city which is brimming with beautiful homes, and brightly coloured flowers. To the back of City Hall, lies the Springer Market Square which hosts a vibrant market Tuesday, Thursday and Saturday. And every Thursday night in the summer a different movie is played in the square. Locals gather with camp chairs to enjoy the show. As for the winter, the square is turned into a skating rink, which looks like something straight from a film.
In summer, there a variety of festivals and events as well as promenades when Princess Street, the main drag, shuts down vehicle traffic to pedestrians. Families, couples, strollers and dogs take over. It's heartwarming. Likewise, Kingston has the highest number of restaurants per capita in all of Canada, and many of them, along with a number of bars, coffee shops and ice cream parlours, are within easy walking distance of one another in the downtown core. That's a whole other blog.
Come to Kingston and get lost in the limestone, the water, the flowers and plenty of great eats!
