A Summer Weekend in Kingston: Three Days of History, Ghosts, and Sunsets
Some trips leave you with tired feet, while others leave you with stories you want to tell again and again.
My late-August weekend trip to Kingston with my mate turned out to be the latter — a mix of history, relaxation, spontaneity, and little moments I’ll treasure for a long time to come.
Day 1: Ghosts, Music, and an Unexpected Karaoke Debut
We set off early on a Saturday morning, bags packed and excitement high. The bus ride from Ottawa was short but filled with anticipation. By the time we dropped our bags at our Airbnb, the city felt ready to be explored.
After wood-oven pizza and lemonade (the kind of hearty meal that instantly makes you feel on vacation), we picked up our Kingston Passes and started wandering through downtown.
The first stop: the Great Lakes Museum, home to the S.S. Keewatin, the last Edwardian-era passenger liner in the world. Standing on its decks felt like brushing against a piece of frozen time.
Later, we joined a walking tour led by Arthur Milnes, who filled the streets with stories of markets, politics, and Kingston’s role as Canada’s first capital. And then came the highlight — the Ghost Trolley Tour. A red tram carried us into Kingston’s eerie past, from Fort Henry to the infamous penitentiary. As the sun dipped, the city’s shadows came alive with tales of hauntings and lost lives.
We ended the night at a cozy pub with karaoke echoing in the background. I hadn’t planned to sing, but with my buddy’s persuasion, I gave it a shot. To my surprise, I not only sang but was chosen as a finalist in their competition. My shaky rendition of Miley Cyrus’s The Climb was met with claps and smiles — a small, unexpected joy of the trip.
Day 2: Towers, Cells, and Sunset on the River
The next morning, we hopped on the city’s trolley tour, a breezy way to circle Kingston’s landmarks. From the Murney Tower to Bellevue House, from Queen’s University’s limestone buildings to the Penitentiary Museum — each stop added another layer to Kingston’s character.
The real standout was the guided tour of Kingston Penitentiary. Walking through its cold corridors, hearing stories of escapes and inmates, felt heavy but fascinating. By the time we stepped out into the daylight, I was both grateful and reflective.
That evening, Kingston outdid itself. We boarded the Island Star for a Thousand Islands dinner cruise. Chicken parm, cheesecake, and chilled drinks were just the beginning. The real feast was the view: islands scattered like emeralds across the St. Lawrence, and a sunset that seemed to linger just for us. We kept sneaking up to the top deck, soaking in every pastel shift of the sky.
Back at the Airbnb, a warm bubble bath wrapped up the day for me — a little ritual of slowing down before reading in bed and falling asleep.
Day 3: Forts, Farewells, and One Last Slice of Pizza
On our last morning, we packed up but weren’t ready to say goodbye just yet. The trolley took us again, this time to Fort Henry, where cannons, soldiers’ quarters, and sweeping views reminded us of Kingston’s strategic past. Standing there, looking out at the meeting of the Cataraqui River and the St. Lawrence, I felt connected to a much older Canada.
Before catching our bus back, my pal and I lounged by the lakeshore, snapped a few garden photos at our Airbnb, and made one final stop at Atomica for pizza and drinks. It felt like the perfect closing note — simple, delicious, grounding.
Looking Back
When we finally reached Ottawa that evening, I felt more energized than when we had left. Kingston had given us three days of stories: some thrilling (ghosts and jails), some romantic (cruises and sunsets), and some hilariously personal (my surprise karaoke debut).
Travel isn’t just about the places you see; it’s about the moments that stick. And Kingston gave me plenty of those.
I can’t wait to plan the next trip — knowing that, once again, the best memories might be the ones we didn’t expect.
Practical Tips for Kingston Visitors
If you’re planning your own getaway to Kingston, here are a few tips we picked up along the way that might help you make the most of your trip.
1. The Kingston K-Pass
If you’re in Kingston for more than a day, the K-Pass is worth every dollar. It bundles entry to museums, heritage sites, trolley tours, and even discounts at local restaurants. It saves both time and money while making sure you don’t miss key attractions.
2. Book the Dinner Cruise Early
The 1000 Islands Dinner Cruise is one of the most popular experiences. Book well in advance, especially during summer weekends. Opt for the evening cruise if you want to catch the sunset — it transforms the whole experience.
3. Hop-On Hop-Off Trolley
The trolley is the easiest way to explore without worrying about parking. It covers City Hall, Bellevue House, Fort Henry, the towers, and Queen’s University.
Pro tip: Sit on the right side of the trolley for better views of the waterfront.
4. Walking Tours
Don’t skip the local guides. Kingston has excellent storytellers — like Arthur Milnes — who make the city’s history come alive. If you enjoy ghost stories, the Ghost Trolley Tour is equal parts spooky and fascinating.
5. Food & Drinks
Kingston’s downtown is packed with great pubs, pizzerias, and patios. Wood-fired pizza is a must-try, and places like Atomica are perfect for a casual but memorable meal. If you’re into pubs, many host live music or karaoke nights — you might even surprise yourself on stage.
6. Airbnb Location
Try booking your stay close to downtown. Most attractions, eateries, and the waterfront are within walking distance, so you’ll save on transport and get more time to explore.
7. Fort Henry Timing
Give yourself at least 2 hours at Fort Henry. There’s more to see than you’d expect — from military history to panoramic views of the St. Lawrence. Early mornings or late afternoons are less crowded.
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