Reading · Road Trip Ontario

Last week I was in Richmond, BC at the Travel Media Association of Canada (TMAC). What a magical place the west coast is from that Indigenous and Japanese history to arguably the best salmon although is an ongoing debate with the east coast. Richmond is a coastal gem where Japanese heritage in Steveston meets a world-class Asian culinary scene, highlighted by the massive Night Market and the legendary “Dumpling Trail.” Between historic shipyards and the Gulf of Georgia Cannery, we bonded over local brews at Fuggles and high-energy karaoke nights. My song of choice for the evening: “Don’t Stop Believin’” by Journey…now i got that song in your head! ;)

Not to dive too deep into the conference but it involves a marathon of meetings with tourism boards in hopes that i can set up some campaigns which would give me the pleqasure of share more exciting places within and around the province with you! We connected with Ontario Resorts, Hamilton, Peterborough, Muskoka, Thunder Bay, North Bay and North Eastern Ontario, and the Bay of Quinte. We even crossed provincial lines to sit down with our neighbors in Quebec (including the Eastern Townships, Outaouais, Charlevoix, Tremblant, and the Laurentians) and Manitoba (Gimli & Hecla, Interlake, Icelandic heritage sites, and Winnipeg). So hopefully everything pans out but since the next big conference will be held in Kingston, I decided to unpack that incredible city and former capital of Canada for this edition

One more thing: This year’s conference was extra special because I walked away with First Place for the Host Destination Story at the TMAC Awards Gala! It’s an honour to be recognized for the stories we tell across the Rudderless Travel and Road Trip Ontario outlets, and it only motivates me to keep digging deeper into the soul of every place I visit, then unpack them with you!

In this edition:
👉🏾 We unpack the Limestone City.
👉🏾 I share my Five Faves for a perfect weekend.
👉🏾 Pro tips on preparing for your summer road trips.

When I think of Kingston, I hear Gord Downie and The Tragically Hip. I’ve got ‘Bobcaygeon’ playing as I write this, which is the perfect soundtrack for a stroll through the Limestone City.

Walking downtown feels like a face-to-face meeting with history. The grand 19th-century limestone heritage buildings aren’t just pretty; they’re the literal architecture of Canada’s first capital. You’ve got these iconic spots like Fort Henry, where sunset ceremonies take place on ramparts once meant to stop an American invasion (damn that feels a little too coincedental at the moment), and the Kingston Pen, the oldest maximum-security prison that once housed the nation’s most notorious criminals. It’s a gritty mix of ivy-covered Queen’s University walls and the crisp air of the boardwalk where the St. Lawrence empties into Lake Ontario.

The city earned its “Limestone” moniker from the local stone used to build its most famous structures. As the capital of a united Canada from 1841 to 1844, it was designed for power and defense, a legacy seen today in the Martello towers and massive fortifications that earned it UNESCO World Heritage status. But it’s not all old stone and grim history. There’s a modern pulse here fueled by a vibrant culinary scene and its role as the gateway to the 1000 Islands. So whether you’re like me and simply looking for a secret patio or prepping for a boat tour, Kingston finds the sweet spot between the past and the present.

Kingston Penitentiary: You have to go “straight to jail” for a tour of Canada’s oldest and most notorious reformatory. It is chilling, fascinating, and an absolute must-see. It could very well be one of the best tours I’ve ever taken. The stories are incredible, but the best part for me was that as you approach various sections of the prison, former employees who worked in those very areas show up to share their firsthand experiences. It adds so much weight to the overall narrative—it simply can’t be beat.
Fort Henry: A living history museum where you can experience 19th-century military life. The view of the city from the hilltop is the best sight for your eyes, and if you time it right, you can catch the Fort Henry Guard during their live marching rehearsals and rifle drills!
Pan Chancho Bakery: A European-style bakery that is a sensory overload. This is the place to grab a bag of treats for your walk along the water. They specialize in incredible artisanal breads, delicate pastries, and towering cakes, but the “secret weapon” is their gourmet grab-and-go deli items.
Kingston Brewing Company: This is the “OG” of Ontario craft beer. It’s the province’s oldest brewpub and Canada’s oldest wine-producing pub. They make everything from scratch on the premises; beers, wines, ciders, and even soda pops. The building was once a telegraph office, and they still use the original vaults today!
Wolfe Island Ferry & 1000 Island Cruises: Take the free ferry ride across the water for a stunning perspective of the Kingston skyline—it is the most relaxing pit stop in the province. If you want the full experience, book a 90-Minute Kingston Discovery Cruise (248 Ontario St). It weaves past National Park Islands and Historic Sites with a lively narration that explains why this city is the heart of the St. Lawrence.

Pro Tip: For a real “wow” factor, check out the 1000 Island helicopter tours to see the islands from above.

👉🏾 40 Fun Things To Do In Kingston, Ontario (Weekend Guide)

👉🏾 Amazing Places To Stay In Kingston, Ontario

Camping season is officially upon us! Don’t be the person who realizes they forgot the stove fuel 100km from the nearest town. We just added the “Camping Essentials Checklist” to the store for only $6.96—the perfect way to ensure your next Ontario adventure is stress-free.
👉🏾 Get the Checklist Here

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If you were “locked up” for a night, would you rather stay in a cell at the Kingston Pen or a haunted heritage hotel downtown? Tell us your choice in the comments!

Kingston: Why Ontario’s Oldest Brewpub belongs on your Summer Hit List! 🍺

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