The cheapest and fastest trains from Bridgeport, CT to Windsor, CT
Cheapest price
$36
Average price
$184
Fastest journey
1 h 29 m
Average duration
1 h 33 m
Trains per day
5
Distance
89 km
The best way to find a cheap train ticket from Bridgeport, CT to Windsor, CT is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Bridgeport, CT to Windsor, CT will cost around $184 if you buy it on the day, but the cheapest tickets can be found for only $36.
It's difficult to get from Bridgeport, CT to Windsor, CT without transferring at least once.
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Travel Information
Compare bus and train for Bridgeport, CT to Windsor, CT
Omio recommends booking the train as it is the most popular option from Bridgeport, CT to Windsor, CT among Omio's users. If you are prioritising price take the bus with prices starting from $18. For those with little time consider booking a train which can get you there in 1h 38m. The ticket price range depends on the travel mode: a bus costs an average of $18, and a train costs an average of $24.
Distance: 55 miles (89 km)
Compare train with
Most popular Train | Bus |
|---|---|
$24 Average price | $18 Average price Cheapest |
2h 8m Average total duration Fastest 1h 38m Onboard + 30m Additional time* | 2h 20m Average total duration 1h 50m Onboard + 30m Additional time* |
Direct Options | Direct Options |
Live departures
Bridgeport, CT to Windsor, CT train times
The table below shows live departures for Bridgeport, CT to Windsor, CT trains for tomorrow, Saturday, March 21. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 8:18 AM Bridgeport, CT | 1h29 | 9:47 AM Windsor, CT | 1 transfer | |
![]() | 10:24 AM Bridgeport, CT | 1h29 | 11:53 AM Windsor, CT | 1 transfer | |
![]() | 2:16 PM Bridgeport, CT | 1h37 | 3:53 PM Windsor, CT | 1 transfer | |
![]() | 4:16 PM Bridgeport, CT | 1h37 | 5:53 PM Windsor, CT | 1 transfer | |
![]() | 5:46 PM Bridgeport, CT | 1h48 | 7:34 PM Windsor, CT | 0 transfersDirect |
Find all the dates and times for this journey
Compare prices and tickets Bridgeport, CT to Windsor, CT by bus or train
Compare bus and train prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
Mar 22
Mar 23
Mar 24
Mar 25
Mar 26
Mar 27
Mar 28
Journey information
Overview: Train from Bridgeport, CT to Windsor, CT
Trains from Bridgeport, CT to Windsor, CT run on average 9 times per day, taking around 1h 38m. Cheap train tickets for this journey start at $24 (€20) but you can travel from only $18 (€14) by bus.
There are 2 trains per day. The earliest train runs at 04:41, the last at 22:12. The fastest train covers the 55 miles (89 km) distance in 1h 34m.
Distance 55 miles (89 km) |
Average train duration 1h 38m |
Cheapest ticket price $24 (€20) |
Trains per day 9 |
Direct trains 2 |
Fastest train 1h 34m |
First train 04:41 |
Last train 22:12 |
Train companies: Amtrak, Metro-North Railroad (MNR) from Bridgeport, CT to Windsor, CT trainsAmtrak, Metro-North Railroad (MNR) trains will get you between Bridgeport, CT and Windsor, CT from $18 (€14). With over 1000 travel companies on Omio, you can find the best train times and tickets for your trip.
Amtrak
Metro-North Railroad (MNR)
FAQs: Trains from Bridgeport, CT to Windsor, CT
Find answers to the most common questions about traveling from Bridgeport, CT to Windsor, CT by train. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest train, the cheapest option, or tips for making the most of your visit at Windsor, CT, this guide helps you travel smarter and with confidence.

popular train stations
Popular train stations from Bridgeport, CT to Windsor, CT
- 5:00 AM - 10:00 PM Monday - Sunday
- Free
- Parking is available 7 days a week with access from Water Street.
- Ralph 'n' Rich's
- Boca Oyster Bar
- Outside the main entrance.
- Ramps, restrooms.
- $0.50
- Holiday Inn Bridgeport-Trumbull-Fairfield
- Hampton Inn by Hilton Shelton
- Quality Suites
- Located in the main hall
- Located in the main hall
- Free
- The station has a main concourse with access to platforms and ticketing services.
- Bus: Greater Bridgeport Transit (GBT) buses available
- Ferry: Bridgeport & Port Jefferson Ferry nearby
Most popular train connections from Bridgeport, CT
More options for your journey from Bridgeport, CT to Windsor, CT
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