Pickering
Pickering
Windsor
Windsor
Train Driving

Pickering to Windsor

Updated: 28 May 2026

Windsor is located approximately 380 kilometers from Pickering. The most popular way to travel is by VIA Rail from Union Station, which takes about 4.5 hours. Driving via Highway 401 takes about 4 hours. Windsor is famous for its proximity to Detroit and its waterfront parks.

Total Distance: 380 km driving distance; 350 km straight-line air distance.
Fastest Way
Driving is slightly faster, but the train is more relaxing.
Cheapest Way
VIA Rail is often cheaper than driving when considering fuel and parking.
Compare Pickering to Windsor Routes
Train
Connecting
Driving
Direct
Duration 4 hours 30 mins 4 hours
Avg Price $60 - $120 $60 - $90 in fuel
Operator VIA Rail Personal Vehicle
Route Lakeshore East to Union, then VIA Rail to Windsor. Highway 401 West.
Tip Book in advance for the best 'Escape' fares. The 401 can be busy; check for construction near London.
Travel Tips
  • Border Crossing
    If you plan to cross into Detroit, bring your passport.
  • Walking
    The riverfront is very walkable; wear comfortable shoes.
  • Parking
    Parking in downtown Windsor is generally affordable.
  • Train
    VIA Rail offers comfortable seating and free Wi-Fi.
  • Weather
    Windsor has a mild climate; pack for summer weather.
Safety Tips
  • Road Safety
    Be careful on the 401 during bad weather.
  • Pedestrian Safety
    Watch for traffic in the downtown area.
  • Emergency
    Windsor has excellent emergency services.
  • Flight Safety
    Follow all airline regulations if flying.
People Also Ask
  • How long is the train?
    About 4.5 hours from Toronto to Windsor.
  • Is it better to drive or take the train?
    The train is more relaxing and avoids highway traffic.
  • Do I need to speak French?
    No, English is the primary language.
  • What is the best time to visit?
    Summer for the best weather and waterfront activities.
  • Is Windsor safe?
    Yes, it is a safe and welcoming city.
Quick Info
  • From Pickering, Ontario, Canada
  • To Windsor, Ontario, Canada
  • Modes
Best Time to Travel

June to August for the best weather and waterfront activities.

Things to Do in Windsor
1
Windsor Riverfront
Walk along the riverfront park with views of the Detroit skyline.
2
Jackson Park
Visit this beautiful park with its famous sunken gardens.
3
Peche Island
Take a boat to this island for hiking and nature trails.
4
Art Gallery of Windsor
Explore the art exhibits in this gallery overlooking the river.
Tags
Pickering to Windsor train to Windsor driving to Windsor Windsor travel Pickering to Ontario Canada travel Windsor commute traveling to Windsor