Is there a direct train?

No, you must transfer at New Haven Union Station.

How long is the drive?

Approximately 75 minutes under normal traffic conditions.

No, there are no tolls on Connecticut highways.

What is the best time to leave?

Mid-morning or mid-afternoon to avoid rush hour.

Is the train reliable?

Yes, the Hartford Line is generally punctual for commuters.

Windsor

Bridgeport

Train Driving

Windsor to Bridgeport

Updated: 29 May 2026

The journey from Windsor to Bridgeport covers approximately 65 miles through the heart of Connecticut. You can drive via I-91 South to I-95 South, which typically takes 75 minutes depending on traffic near New Haven. Alternatively, the Hartford Line train offers a reliable public transit option connecting Windsor Station to Bridgeport Station. This route passes through major hubs like Hartford and New Haven. Expect heavy congestion during weekday rush hours near the I-91 and I-95 interchange.

Total Distance: 105 km driving distance; 90 km straight-line air distance.

Fastest Way

Driving via I-91 and I-95 is the fastest, taking 75 minutes outside of peak traffic hours.

Cheapest Way

Driving is the cheapest option if traveling with passengers, costing roughly $15 in fuel.

Compare Windsor to Bridgeport Routes

	Train Connecting	Driving Direct
Duration	2 hours	1 hour 15 minutes
Avg Price	$18-$25	$15-$20 in fuel
Operator	Hartford Line / Metro-North	Personal Vehicle
Route	Windsor Station to New Haven Union Station, transfer to Metro-North.	I-91 South to I-95 South via New Haven.
Tip	Purchase a combined ticket to save on transfer fees.	Avoid the I-91/I-95 interchange in New Haven between 4 PM and 6 PM.

Travel Tips

Check Traffic
Use real-time apps to monitor the I-91/I-95 interchange status before departing.
Train Tickets
Use the CTrail eTix app to purchase your Hartford Line tickets in advance.
Parking
Bridgeport downtown parking garages are safer and more convenient than street parking.
Off-Peak Travel
Travel between 10 AM and 2 PM to avoid the worst of the Connecticut highway congestion.
Station Safety
Always wait in well-lit areas at the Windsor train platform during evening hours.

Safety Tips

Highway Vigilance
Stay alert for sudden braking on I-95 near New Haven due to high traffic volume.
Vehicle Prep
Ensure your tires are properly inflated for the long highway stretch.
Emergency Kit
Keep a basic emergency kit in your trunk, including water and a flashlight.
Night Driving
Avoid driving late at night on I-95 if you are prone to fatigue, as the road is heavily trafficked.