Driving
Chester to Windsor
Updated: 30 May 2026
The drive from Chester to Windsor is a 60-kilometer trip along Highway 14. It takes approximately 45 minutes. Windsor is a historic town in the Annapolis Valley, known for its connection to hockey and its beautiful scenery. The drive is scenic and connects you to the valley region.
Total Distance: 60 km driving distance; 45 km straight-line air distance.
Fastest Way
Driving is the fastest method, taking 45 minutes.
Cheapest Way
Driving your own vehicle is the most practical method.
Compare Chester to Windsor Routes
Driving
Direct
Duration
45 mins
Avg Price
8-12 CAD
Operator
Personal Vehicle
Route
Highway 14.
Windsor is the birthplace of hockey.
Travel Tips
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TrafficTraffic is generally light.
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ParkingParking is generally available.
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NavigationThe route is very simple.
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WeatherEnjoy the valley breeze.
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ServicesWindsor has all the services you need.
Safety Tips
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HighwayStay alert on the highway.
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PedestriansWatch for pedestrians in town.
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EmergencyKeep your phone charged.
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DrivingFollow all traffic laws.
People Also Ask
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Is there a bus?No, you need a car.
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How long is the drive?About 45 minutes.
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Is it a toll road?No, it is toll-free.
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Can I walk?No, it is too far to walk.
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What is the best way?Driving is the best way.
Quick Info
- From Chester, Nova Scotia, Canada
- To Windsor, Nova Scotia, Canada
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Modes
Best Time to Travel
Anytime, especially in autumn for the harvest.
Things to Do in Windsor
1
Hockey Heritage Centre
Learn about the history of hockey.
2
Fort Edward
Visit the historic fort.
3
Shopping
Visit the many stores in the area.
4
Dining
There are many restaurants to choose from.
Tags
Chester to Windsor
Windsor travel
Nova Scotia transit
Highway 14
Annapolis Valley
Chester to Windsor drive
Nova Scotia road trip
scenic Nova Scotia
