The average train between Windsor and Montauk takes 7h 10m and the fastest train takes 6h 28m. The train service runs several times per day from Windsor to Montauk. 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 3 times a day between Windsor and Montauk. The earliest departure is at 6:14 AM in the morning, and the last departure from Windsor is at 8:04 PM which arrives into Montauk at 3:31 AM. All services require a transfer at New Haven and take an average of 7h 10m. The schedules shown below are for the next available departures.



6h 28m • 3 changes



7h 18m • 3 changes
Arrives next day



7h 53m • 3 changes



6h 28m • 3 changes



7h 18m • 3 changes
Arrives next day



7h 53m • 3 changes



6h 28m • 3 changes



7h 18m • 3 changes
Arrives next day



7h 53m • 3 changes



6h 28m • 3 changes



7h 18m • 3 changes
Arrives next day



7h 27m • 3 changes
Want to know about travelling from Windsor to Montauk? 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 Montauk. However, there are services departing from Windsor station and arriving at Montauk station via New Haven. The journey, including transfers, takes approximately 7h 10m.
Windsor to Montauk train services, operated by Amtrak, depart from Windsor station.
Windsor to Montauk train services, operated by Amtrak, arrive at Montauk station.
The distance between Windsor and Montauk is 108 km. The road distance is 378 km.
You can take a train from Windsor to Montauk via New Haven, Ny Moynihan Train Hall At Penn Station, New York Penn Station, and Jamaica in around 7h 19m.