3 Ways to Cruise Kingston

Whether you're touring by motorcycle, boat, or trolley, Kingston offers great places to stay, places to dine, things to see, and roads—or waters—to travel.

Years ago, the annual HOG rally brought me to Kingston for my first time ever. At that time, the streets of this small city in this region of majestic waterways, South Eastern Ontario, were overcome by thundering Harley Davidsons from across North America. Of all the cities this infamous rally could be hosted in, Kingston was the chosen one. At the time, I didn’t know enough about Kingston to speculate as to why the iconic Harley Davidson brand chose this location to host their massive event—however, after visiting the city a few years later for the second time, I now understand. While Kingston may no longer be Canada’s capital city (that changed in 1944), I think it’s fair to say that it has now become the unofficial cruising capital of Ontario.

Let’s think about this for a minute: there are lots of cities in Ontario and even Canada that are home to thousands of bikers and tons of great motorcycle touring, so why would I go to such lengths as to name Kingston as Ontario’s cruising capital? And why would Harley Davidson choose to associate their name with this city? Well, just like the motorcycle brand, Kingston is full of rich history and culture, with great pride, loyalty, and honour to those who fought for, and paved the way for its future. There is certainly something special about Kingston, from the old limestone buildings, to its central location on the St. Lawrence River, the people who live there, the unreal restaurants and shops that make up the downtown core, and—of course—the events that are hosted there throughout the year. All of this is within a few hours of Toronto.

Celebrating Canada's 150th in Kingston, Ontario.

While I’m certainly partial to motorcycles, I realized that Kingston offers its visitors a number of ways to cruise around and explore. Its proximity to a number of fun motorcycle routes that run along Ontario’s waterfront trail and expand into Quebec are an added bonus. Plus, visitors can also cruise at least three ways: by motorcycle, boat or streetcar. That right there is what I believe makes Kingston Ontario’s unofficial cruising capital.  

Check out the trip ideas below to plan your next adventure to Kingston!


Since my last visit to Kingston on a Harley Davidson V-Rod, it’s now become a tradition that I ride a Harley in Kingston. So here I was mid-summer this year, on a Harley Davidson Street Glide, from MotoSport Plus in Kingston. The bike was everything I needed and more; a couch on wheels complete with half fairing, ample space in the side cases for my extra gear, speakers, cruise control, and—of course—those throaty pipes that command attention on the road… Sorry, let me wipe the drool from my face here… 

The MotoSport Plus showroom has everything the Harley enthusiast could want and more!

Ben at MotoSport Plus helped me plan out a few routes to take on this trip. With so many to choose from, I stuck with shorter routes to balance my trip out and to make sure I had time for some of the other activities I enjoy.

Ben at MotoSport Plus gave me some tips on where to ride.


Loyalist Parkway: Early one morning, I took advantage of the beautiful weather and quiet roadways to cruise on my Street Glide down Highway 33, also known as the Loyalist Parkway. This route offers beautiful waterfront views for the majority of the ride, along with winding roads, and several spots to pull off for a rest of photo opp. Riders can take a ferry to Glenora, and then continue along the 33 to Picton, which is a good place to stop for a coffee or snack. 

Highway 33 West is a great ride along Ontario’s Waterfront Trail

Rideau Heritage Route: This route takes riders along some great twisty roads, around lakes and through cottage country. With several different options, riders can customize their route to take them either a shorter or longer distance. I rode along highway 10 up to Westport, and then took highway 32, 15, and then 11 back to Kingston. Overall my route took me a few hours and got me back to the area before lunch.

The Harley Davidson Street Glide on the Rideau Heritage Route.

There are many other motorcycle route options to check out too!


Delta Hotels Kingston Waterfront: Guests can’t get over the unreal waterfront view at this hotel. Since I got up early to ride each day, I was able to take in the beautiful sunrise over the water. Comfy beds and all the amenities I needed ensured I was rested and ready to ride. The hotel also offers a paved, covered lot which is great for bikers staying overnight.

The Delta is an ideal place to stay given its central location to the Kingston downtown core. 
A waterfront view at this hotel offered the most beautiful sunrises each morning.
A comfortable king bed is in order after a day of riding.


Morrisons (Breakfast): This place is your classic old-school diner. Expect to get quick service at an affordable cost. If you are looking for a simple bacon and egg breakfast, or other breakfast staples, this is the place to fill your belly before riding. 

Off to Morrison's for breakfast. Photo: Dave Kellem

Sir John’s Public House or The Kingston Brewing Company aka the “Brew Pub” (Dinner):

Sir John’s is a neat, historic spot to spend a few hours after a long day of riding or sightseeing. The building was the law office of our first Prime Minister, John A. McDonald, from 1849 to 1860 and features great local and imported beers in addition to delicious meals like fish ‘n’ chips, maple baked salmon, and lamb shank.

The Kingston Brewing Company is Ontario’s oldest brew pub, adding to the city’s history. It offers your typical pub-style foods like poutine, burgers, sandwiches, and brisket. That said, don’t mistake this place for a typical greasy spoon restaurant, as meals are absolutely delicious and the menu offers salads and other lighter meals for those looking for a smaller lunch or dinner. 


The Motorcycle Show 'N Shine / Freestyle Show:

I attended this event years ago and I’m convinced it just keeps getting bigger and better. This year marked the 10th anniversary of the event, which brings thousands of bikers to the city to showcase their rides while supporting the local Almost Home charity. The event features Jason Thorne’s freestyle motocross show as one of the main attractions, in addition to the show & shine. Add a vendor area and waterfront band and you’re set!

This year marked the 10th anniversary of the Kingston Motorcycle Show 'N Shine. 
Riders from all over Ontario and beyond attended the rally which benefitted a local charity.
The Jason Thorne Freestyle Motocross show is a well attended event for motorcycle enthusiasts. 


If you don’t ride a motorcycle, or just need to mix things up, check out the Kingston 1000 Islands Cruises. This is hands-down the best way to get a full tour of the Thousand Islands by water. I hopped aboard the Island Queen for a brunch cruise, which was a beautiful three-hour tour of the Thousand Islands region. The cruise provides live music and a commentary about each area we cruised through, which gave me the opportunity to learn more about the history of the islands. I munched on a light brunch, chatted with fellow travellers, and had time to relax.

A tour of the thousand islands by boat was the best way to take in the sights of this area.

The company that runs the cruise line offers a variety of options for travellers, including dining cruises, sightseeing cruises, and private charters. The Island Queen cruise ship that I was on had three levels, and the view from every level and window was absolutely gorgeous.

Brunch cruise on the Island Queen was the perfect way to start my Sunday!


Dianne’s Fish Shack & Smokehouse (Dinner): If you decide not to take a dinner cruise, check out Dianne's, which is located just down the street from the Delta Waterfront hotel and Kingston cruise ship area. Whether you dine inside or on the patio, the atmosphere is great and the food is to die for!


With an all-access day pass, the Kingston trolley is a great way to see the city with a tour guide pointing out the must-see areas and providing history. Passengers can get off at nine different stops along the way and get back on later once they’ve had a chance to explore, eat, or shop.

All you need is a day pass and and you're set to tour by trolley. Photo: Kingston Trolley Tours / KingstonTrolley.ca


Pan Chancho (breakfast): Before heading on a trolley tour, I enjoyed a delicious breakfast on the outdoor patio of Pan Chancho. This is another great place to enjoy a meal or grab a pastry for a snack later; I recommend the curry & eggs dish.

Breakfast at Pan Chancho was to die for! Try the Curry & Eggs dish!
Baked goods at the Pan Chancho Bakery are always a nice treat or snack.

Chez Piggy, Casa Domenico or Le Chien Noir (dinner): After a full day of trolley riding and adventures, enjoy an evening out or a date night dinner at one of these fabulous locations—all come highly recommended. 

The inviting entryway to Chez Piggy is just the beginning. This restaurant is a local favourite in Kingston.
A delicious steak dinner after cruising around Kingston.


Here are a few places I stopped at along the Trolley tour:

Fort Henry

Enjoy a guided tour of the Fort, or take in the Garrison Parade. The Fort has so many different activities to offer, including ghost tours and learning how to fire a rifle. The gift shop and bakery are must-stops; I recommended trying the homemade bread if you have the chance! Before heading back to the Trolley, I grabbed lunch at the Battery Bistro patio restaurant which offers a great view of Lake Ontario.

Watching soldiers at Fort Henry march throughout the grounds.

Market Square

Located in the heart of Kingston, there always seems to be something going on at Market Square. You can visit the Public Market, Ontario’s oldest market, established in 1801. There’s also the close-by Martello Alley, for the art lovers out there. If you’re in town on a Thursday night, you check out the weekly movie. There are also always nearby events like the annual Taste of Kingston or Show & Shine— there really is something for everyone!

The downtown core is always busy with events throughout the year including Taste of Kingston!

Bellevue House

This National Historic Site was once Sir John A. McDonald’s home. Nestled among an apple orchard and huge oak trees, this restored home offers guests a guided tour, in addition to other activities like whiskey tasting and a fall harvest festival. I learned a lot about our country’s history from this tour; it’s a must-visit on the Trolley Tour!

Nestled among an apple orchard and oak trees is a house where our first Prime Minister lived.
A guided tour was a great way to learn more about our country’s history.

The trolley makes lots of other interesting stops, which you can check out online before booking. 

End your day with a show at the Isabel Bader Centre for the Performing Arts. This newly built centre is one of a kind, featuring a world renowned design that takes into consideration acoustics and sound production to deliver captivating line-up of performances that will knock your socks off. 

There you have it! Three ways to cruise in Kingston, each offering a different and unique way to take in all that the city has to offer. For more information about this city, you can visit the city's official website or stop in at the Visitor Information Centre while you are there.

About Jess Kline

Jess is a long-time motorsports enthusiast and promoter. She is owner of Backwoods Promotions, which specializes in motorsports, automotive & outdoors event staffing and marketing. When she isn't hard at work, Jess enjoys exploring the Backwoods of Ontario, whether riding her Suzuki SV650 down a winding road, or getting out on an ATV, snowmobile or boat! 

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