The average train between Windsor and Middletown takes 4h 53m and the fastest train takes 4h 21m. The train service runs several times per day from Windsor to Middletown. The journey time may be longer on weekends and holidays; use the search form on this page to search for a specific travel date.
Trains run every 4 hours between Windsor and Middletown. The earliest departure is at 4:41 AM at night, and the last departure from Windsor is at 8:04 PM which arrives into Middletown at 12:31 AM. All services require a transfer at New Haven and take an average of 4h 53m. The schedules shown below are for the next available departures.


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4h 44m • 2 changesWant to know about travelling from Windsor to Middletown? We have put together a list of the most frequently asked questions from our users such as: What is the cheapest mode of transport? What is the quickest option? How much do tickets usually cost? and many more.
No, there is no direct train from Windsor to Middletown. However, there are services departing from Windsor station and arriving at Middletown Nj station via New Haven station and Ny Moynihan Train Hall At Penn Station. The journey, including transfers, takes approximately 4h 53m.
Windsor to Middletown train services, operated by Amtrak, depart from Windsor station.
Windsor to Middletown train services, operated by NJ Transit, arrive at Middletown Nj station.
The distance between Windsor and Middletown is 203.8 km. The road distance is 254 km.
You can take a train from Windsor to Middletown Nj via New Haven, Ny Moynihan Train Hall At Penn Station, and New York Penn Station in around 4h 56m.