Last Updated on March 22, 2025
So, you’re planning a road trip from Toronto to Windsor? Great choice! This Southern Ontario route may not be as long as some epic cross-country journeys, but don’t underestimate its charm. From vibrant cities and charming small towns to sprawling vineyards and picturesque lakeshores, this trip has everything you need for an unforgettable adventure. Ready? Let’s hit the road!
Road Trip Planner
Overview
This route spans approximately 395 km and offers a combination of city stops, historical sites, and natural beauty. It’s a pleasant drive with plenty to see and explore along the way!
Road Trip Key Details
Distance: Approximately 395 km.
Driving Time: About 4 to 5 hours (without stops).
Routes:
Main Route: Take Highway 401 (direct and fast).
Scenic Option: Follow Lake Erie’s shoreline for picturesque views.
Best Time to Go: Spring to Fall for pleasant weather and outdoor activities.
| LEG | FROM | TO | DISTANCE | HIGHLIGHTS |
|---|---|---|---|---|
| 1 | Toronto | Mississauga | 30 km | Square One Shopping Centre, Streetville |
| 2 | Mississauga | Hamilton | 45 km | Royal Botanical Gardens, Dundurn Castle |
| 3 | Hamilton | London | 130 km | Fanshawe Pioneer Village, scenic drive |
| 4 | London | Chatham-Kent | 110 km | Rondeau Provincial Park, cultural and agricultural heritage |
| 5 | Chatham-Kent | Windsor | 80 km | Point Pelee National Park, Detroit River waterfront |
| QUICK LINKS | |
|---|---|
| Why This Trip is a Must-Do | Arriving in Windsor |
| Tips for a Safe and Enjoyable Trip | Southern Ontario’s Flavours |
| Getting Started: Planning the Journey | |
| Stops Worth Taking Along the Way |
Why This Trip is a Must-Do
This trip covers about 395 km via Highway 401, making it a manageable drive of approximately 4 to 5 hours without stops. But where’s the fun in that? Whether you’re a first-time road tripper or a seasoned explorer, this route offers something for everyone. The real magic happens when you take your time and explore the gems along the way. Southern Ontario is rich in history, culture, and natural beauty—perfect for those who love a mix of urban and rural vibes.
So, what are you waiting for? Fill up the tank, grab some snacks, and let the open road lead the way. Happy travels!
Tips for a Safe and Enjoyable Trip
Before you hit the road, here are some final tips to make your trip smooth and enjoyable:
- Plan Your Stops: Mark your points of interest ahead of time to avoid missing out on anything cool.
- Check Traffic: Highway 401 can get busy, especially near Toronto, so consider leaving early to beat the rush.
- Stay Flexible: The best road trips are the ones where you embrace the unexpected—whether that’s an unplanned stop at a roadside fruit stand or a detour to chase a beautiful sunset.
Getting Started: Planning the Journey
Best Time to Travel
Like most Ontario road trips, summer and early fall are ideal for this journey. The weather is perfect for outdoor activities, and the fall foliage adds a pop of colour to the landscape. Spring is another great option, especially when local farmers’ markets start buzzing with fresh produce. Winter trips are possible too, but make sure your car is ready for snowy conditions.
The Basics
- Distance: Roughly 395 km.
- Driving time: 4-5 hours, not including stops.
Packing Essentials
You won’t need to pack for extreme conditions on this relatively short trip, but here are some must-haves to ensure a smooth ride:
- Snacks (yes, always snacks).
- A solid playlist—some classic Canadian tunes like The Tragically Hip or Rush never hurt.
- A daypack for exploring local attractions.
- A camera or smartphone for capturing memories.
- A reusable water bottle to stay hydrated.
Budgeting for the Trip
This road trip is relatively easy on the wallet, but here’s a quick breakdown of what you might spend:
- Fuel: Gas for the 395-km trip will cost around $50-$75, depending on your vehicle.
- Accommodation: If you’re staying overnight in Windsor, you’ll find options ranging from budget motels to more upscale hotels.
- Food: Allocate around $15-$20 per meal if you’re eating out at casual spots.
- Attractions: Many stops, like parks and small-town sights, are free or low-cost, making this a budget-friendly adventure.
Stops Worth Taking Along the Way
While the drive from Toronto to Windsor can be done in one go, why rush when there’s so much to see? Here are some fantastic stops to make your journey truly memorable:
1. Mississauga
Start your trip with a quick detour in Mississauga. Check out Port Credit, a charming waterfront area perfect for a morning coffee by the lake. If you’re into shopping, Square One Mall offers a range of stores to browse before hitting the road.
2. Hamilton
Known as “The City of Waterfalls,” Hamilton is a nature lover’s paradise. A quick hike at Webster’s Falls or the Devil’s Punchbowl will give you a refreshing start to your journey. If you’re more into history and culture, Dundurn Castle is a fascinating stop.
3. London
Ah, London—Ontario’s very own “Forest City.” Stop here for lunch and explore Victoria Park or the historic Covent Garden Market. If you’re a fan of craft beer, London’s breweries, like Anderson Craft Ales, are a must-visit.
4. Chatham-Kent
As you approach Windsor, make a pit stop in Chatham-Kent to dive into some fascinating history. The area played a significant role in the Underground Railroad, and the Buxton National Historic Site is a moving tribute to this legacy.
5. Point Pelee National Park
This is slightly off the main route, but it’s well worth the detour. Point Pelee is the southernmost point of mainland Canada and a paradise for birdwatchers and nature enthusiasts. Take a stroll along the boardwalk or dip your toes into Lake Erie.
Arriving in Windsor
Congratulations, you’ve made it to Windsor—the “Automotive Capital of Canada” and a city bursting with history, culture, and stunning waterfront views. Here’s what to do once you’ve arrived:
- Explore the Riverfront: Windsor’s waterfront is a highlight, offering panoramic views of the Detroit skyline. Stroll along the Windsor Sculpture Park, where art meets nature, or relax at Dieppe Gardens.
- Visit the Distillery District: Did you know Windsor has a rich whisky-making heritage? Visit the Canadian Club Brand Centre to learn all about it (and maybe enjoy a tasting).
- Take a Step Back in Time: The historic Sandwich neighbourhood is one of Windsor’s oldest areas. Check out the charming buildings, riverside parks, and cozy pubs.
- Indulge in Local Cuisine: Windsor is known for its unique style of pizza—don’t leave without trying it! Local joints like Capri Pizza or Armando’s are excellent options.
- Experience Caesars Windsor: Feeling lucky? Head to Caesars Windsor for some gaming, dining, or entertainment.
Southern Ontario’s Flavours
Foodies, rejoice—this route is packed with amazing culinary experiences. Here are a few regional highlights to look out for:
- Hamilton: Try some classic Canadian comfort food like poutine at a local diner.
- London: Sample artisanal treats from local bakeries or stop by one of the city’s trendy brunch spots.
- Windsor: As mentioned, don’t miss the pizza! Windsor’s unique style is all about shredded pepperoni and fresh ingredients.
Wrapping Up: A Road Trip to Remember
There you have it—a compact but action-packed road trip from Toronto to Windsor. This journey is the perfect blend of city excitement, small-town charm, and natural beauty. Whether you’re exploring waterfalls in Hamilton, indulging in craft beer in London, or soaking in the rich history of Windsor, you’ll find plenty of reasons to fall in love with Southern Ontario.
So, why not turn your next drive into an adventure? Pack your car, bring your sense of curiosity, and embrace all the memories waiting to be made. After all, the road isn’t just a path to your destination—it’s an experience in itself.
