Is there a direct train from Oshawa to Windsor?

No, you must transfer at Union Station in Toronto.

How long is the drive to Windsor?

It takes about 4 to 5 hours depending on traffic.

Can I take a bus to Windsor?

Yes, several bus lines operate from Toronto to Windsor.

Is Windsor worth visiting?

Yes, it has a great waterfront and unique cultural ties to Detroit.

What is the best way to travel to Windsor?

Driving is the most convenient, while the train is the most comfortable.

Oshawa

Windsor

Train Driving

Oshawa to Windsor

Updated: 28 May 2026

The journey from Oshawa to Windsor is a long trek across Southern Ontario, spanning approximately 400 kilometers. Driving via Highway 401 West is the most common method, taking about 4 to 5 hours. For those preferring public transit, VIA Rail offers service to Windsor, though it requires a transfer in Toronto. Windsor is located directly across the border from Detroit, making it a unique gateway city. Plan for a full day of travel if using public transportation.

Total Distance: Driving distance is 400 km; straight-line air distance is 360 km.

Fastest Way

Driving, taking approximately 4 hours and 15 minutes.

Cheapest Way

Bus services like FlixBus, which can be cheaper than the train if booked early.

Compare Oshawa to Windsor Routes

	Train Connecting	Driving Direct
Duration	5 hours 30 mins	4 hours 15 mins
Avg Price	$80 - $150 CAD	$70 - $90 in fuel
Operator	VIA Rail	Personal Vehicle
Route	Train to Union Station, transfer to Windsor-bound train.	Highway 401 West all the way to Windsor.
Tip	The train ride through the agricultural heartland of Ontario is quite scenic.	The 401 ends in Windsor, making navigation very straightforward.

Travel Tips

Border Crossing
If you plan to cross into Detroit, ensure you have your passport ready.
401 Construction
Check for construction updates on the 401, as it is a major highway with frequent repairs.
Windsor Transit
Windsor has a local bus system that connects the main areas of the city.
Dining
Windsor is famous for its pizza; be sure to try a local slice while you are there.
Booking
Book train tickets well in advance to avoid high last-minute prices.

Safety Tips

Long Drive
This is a long drive; stop every 2 hours to stretch and stay alert.
Weather
Windsor can have different weather patterns than the GTA; check the local forecast.
Vehicle Prep
Check your tire pressure and fluid levels before starting this long journey.
Night Driving
Avoid driving the 401 at night if you are tired, as it is heavily used by transport trucks.