There’s something uniquely exhilarating about crossing the border from the U.S. into Canada with a car packed for adventure. On my first road trip to Kingston, Ontario, I remember the thrill of leaving behind familiar highways and entering a land dotted with lakes, historic towns, and wide-open skies. Driving into Kingston isn’t just about reaching a destination; it’s about experiencing the landscape, the rhythm of small towns, and the subtle cultural shift that occurs once you cross into Canada.
The moment I entered Ontario, I felt a sense of anticipation. The roads are well-maintained, the scenery changes from dense forests to open farmland, and every mile seems to promise a story. My first drive was planned from upstate New York, crossing the Thousand Islands Bridge at the Canadian border—a gateway into Eastern Ontario. The view of the islands scattered across the St. Lawrence River was breathtaking. Each one seemed to hold its own secret: a mansion, a lighthouse, a tiny dock. I knew then that Kingston, the Limestone City, would offer a blend of history, culture, and natural beauty that warranted a proper road trip exploration.
Preparing for the Journey
Before starting, I made sure my car was ready for long stretches of driving. I stocked snacks, downloaded offline maps, and prepared a playlist that would carry me through the lakeside roads and countryside turns. For accommodations, I researched hotels and inns on Booking.com, Hotels.ca, and Airbnb, ensuring I had options in Kingston and nearby towns. For flights into Canada in case friends joined me from afar, I checked AirCanada.com, FlairAirlines.com, and Expedia.ca for domestic connections.
Booking tickets for attractions ahead of time is also crucial. I relied on Tiqets and GetYourGuide for sites like Fort Henry and Bellevue House. For restaurants, apps like OpenTable and Yelp helped me snag evening reservations in Kingston’s bustling downtown.
Route 1: Thousand Islands & Waterfront Loop
Distance: ~150 km round trip
Time: Approximately 3–4 hours including stops
This route is perfect for a scenic drive along the St. Lawrence River, offering a blend of natural beauty, historic landmarks, and charming small towns. I started my journey in Kingston, feeling the familiar excitement that comes with a road trip, with a car packed lightly with snacks, a camera, and a sense of adventure. Heading northeast toward Gananoque, often called the gateway to the Thousand Islands, the roads immediately hug the shoreline, offering occasional glimpses of sparkling water through the trees. The light bounced off the river’s surface, creating a sense of anticipation for the stops ahead.
The drive itself is serene, with winding roads that alternate between forested stretches and open vistas. I made a mental note to pull over frequently; every corner seemed to reveal a new photo opportunity, whether it was a glimpse of a distant lighthouse or a quiet dock tucked behind tall reeds. The combination of the St. Lawrence River’s expanse and the scattered islands is truly breathtaking.
Must-See Stops Along the Way
- Thousand Islands Bridge: The first highlight is the Thousand Islands Bridge, a border-crossing marvel connecting New York and Ontario. I paused on the Canadian side to take photos of the river stretching out in both directions. The view is striking—crystal-clear water reflecting the sky, dotted with islands each adorned with quaint homes or private docks. Watching cars slowly move across the bridge, I felt a sense of connection between the two countries, linked by both geography and history.
- Gananoque Waterfront: Upon reaching Gananoque, I found myself drawn to the quaint waterfront area, where small cafés and artisan shops line the street. I parked the car and wandered for a few minutes, soaking in the atmosphere. I grabbed a coffee at a local café, enjoying the aroma of freshly brewed beans while watching boats drift lazily along the water. The town has a slow, welcoming pace, perfect for breaking up the drive.
- Thousand Islands Cruises: No trip along this route would be complete without a cruise. Departing from Gananoque at 1 Brock Street, the cruises provide close-up views of private islands, historic castles, and iconic lighthouses. I booked my ticket through 1000islandscruises.ca for CAD \$45, which included detailed commentary on the history and geography of the area. Gliding past the islands, I marveled at the unique homes perched on their own private plots of land and listened intently to the stories of the area, from early settlers to modern-day conservation efforts.
On the drive back to Kingston, I made a detour to Charleston Lake Provincial Park, a hidden gem that offers panoramic views of a tranquil lake surrounded by gently rolling hills. A short trail led me to a viewpoint, where the water mirrored the vibrant fall foliage. The colors—crimson, amber, and gold—were almost surreal, and I took several moments just to breathe in the crisp air and take photographs. Entry and parking at the park cost around CAD \$10–\$15 per vehicle, a small price for such a serene experience.
This loop is accessible year-round, but I found summer and fall to be the most rewarding. Summer brings warm weather and active wildlife, while fall paints the landscape in dramatic, colorful tones. Winter can be picturesque too, with snow-covered islands, but some areas may have limited access. The combination of winding roads, striking water views, and charming stops makes this route one of my favorite drives in the region.
Route 2: Historic Kingston & Limestone Trail
Distance: ~40 km
Time: Half-day exploration
Kingston itself is compact yet brimming with history. I planned a self-driving route through the city’s historic neighborhoods, focusing on limestone architecture and key landmarks that speak to Canada’s rich past. Driving slowly through the streets, I couldn’t help but notice the unique charm of Kingston’s downtown—the way historic buildings blend seamlessly with modern cafés and shops.
Key Stops
- Fort Henry National Historic Site (1 Fort Henry Drive): Fort Henry is a must-see military fortification dating back to the 19th century. I booked my tickets through Parks Canada at CAD \$20. Walking along the parade grounds, past the barracks and cannons, I felt transported back in time. The fort’s strategic position overlooking Lake Ontario is breathtaking, and during summer, the sunset ceremony adds a dramatic and colorful experience that I found unforgettable.
- Murney Tower (King & Barrie Streets): This small Martello tower offers a quick but meaningful stop. Tickets are CAD \$4, and the tower provides panoramic views of Lake Ontario and the surrounding cityscape. Climbing to the top, I could see the limestone buildings gleaming in the sunlight, and it struck me how much history is packed into such a compact urban area.
- Bellevue House (35 Centre Street): The former home of Sir John A. Macdonald, Canada’s first prime minister, is both educational and charming. Booking online through Parks Canada was seamless, and the guided tour brought the past to life. I wandered through rooms decorated in period furnishings, imagining the daily life of one of Canada’s most influential figures.
- Kingston Waterfront & Confederation Park: No visit to Kingston is complete without a walk along the waterfront. I parked my car and strolled along the piers, taking in the swans gliding across the water, small boats bobbing gently, and the distant hills across the lake. Free public parking made the stop convenient, and the atmosphere was peaceful and rejuvenating.
- Along this route, I stopped for lunch at Chez Piggy (68R Princess Street), reserving my table through OpenTable. The meal was a mix of eclectic flavors, and I enjoyed the cozy, intimate ambiance of the restaurant. It was the perfect complement to the historical exploration of the morning, giving me energy and inspiration for the afternoon.
- This route may be short, but it offers a deep dive into Kingston’s architectural and cultural heritage. The mix of historic landmarks, scenic views, and charming eateries made it an enriching half-day journey that I would repeat in a heartbeat.
Route 3: Kingston to Prince Edward County Wine & Countryside Drive
Distance: ~180 km round trip
Time: Full-day adventure
For a more rural experience, I took a scenic route south toward Prince Edward County. The drive meandered through farmland, vineyards, and rolling hills, with stops at small villages along the way.
Highlights Along the Route
- Waupoos Estate Winery: About 45 minutes from Kingston, this winery offers tastings overlooking Lake Ontario. Tickets for tastings start at CAD \$15. Booking online via WineTourism.ca is recommended.
- Sandbanks Provincial Park: Famous for its sandy beaches and dunes. Entry is CAD \$17 per car. I hiked a short trail, enjoying panoramic lake views that felt almost tropical.
- Picton Village: Quaint shops and cafés line the main street. I parked the car and explored on foot, stopping at a bakery for fresh pastries.
I returned to Kingston in the evening, savoring the sunset over Lake Ontario. The drive reminded me that Ontario is full of hidden gems just an hour or two outside the main cities.
Driving Tips and Reflections
Over the course of my drives, I learned a few lessons that made the experience smoother and more enjoyable:
- Plan for Fuel Stops: Gas stations can be sparse in rural areas, especially along Route 3. I always filled up in towns like Gananoque or Picton.
- Use GPS and Offline Maps: Cellular coverage can be spotty along lakeside roads. Google Maps offline or Waze ensures I didn’t get lost.
- Check for Seasonal Closures: Some attractions, like Sandbanks, are best visited in summer or fall; winter access can be limited.
- Book Ahead: Accommodations in Kingston and nearby towns fill quickly in summer. I used Booking.com, Hotels.ca, and Airbnb to secure rooms with free cancellation options.
- Local Dining Reservations: Restaurants downtown, like Wooden Heads Pizza and Pan Chancho Bakery, can get busy. OpenTable helps lock in a table.
My Personal Reflections
There’s something about driving yourself in Kingston that feels completely freeing. Unlike flying or taking the train, having a car lets you pause wherever you want—an unplanned photo stop along Lake Ontario, a quiet hike through provincial park trails, or a sudden detour to a historic village. I’ve driven these routes multiple times, and each journey has offered something new: a different angle on the Thousand Islands, a hidden café in Prince Edward County, or the golden glow of the sun on limestone buildings downtown.
Booking accommodations, flights, and tickets in advance through Canadian platforms made the experience worry-free. Whether I used Expedia.ca for flights, Hotels.ca for rooms, or Tiqets for attractions, the convenience meant I could focus entirely on the drive itself and the scenery unfolding outside my window.
For anyone starting in the U.S., the border crossing is smooth if you have your documents ready. I typically check AirCanada.com or FlairAirlines.com for Canadian domestic connections if friends are flying in to join me, and use OpenTable for evening dinners in Kingston.
The three routes I’ve detailed—Thousand Islands & Waterfront Loop, Historic Kingston & Limestone Trail, and Kingston to Prince Edward County—each offer a different perspective on the region. Some focus on natural beauty, others on cultural and historical landmarks, and all benefit from the freedom that a car provides.
Driving in and around Kingston feels like a mosaic of experiences: sparkling lakes, centuries-old forts, charming villages, and cozy cafés. Planning ahead using Canadian booking platforms for hotels, flights, and attractions makes everything smoother and allows you to enjoy the moment fully. Each mile traveled along these roads reveals why Kingston is a city worth exploring by car, at your own pace, with freedom to pause wherever curiosity leads you.
