The average train between Southold and Times Square takes 2h 56m and the fastest train takes 2h 38m. The train service runs several times per day from Southold to Times Square. 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 4 times a day between Southold and Times Square. The earliest departure is at 5:31 AM in the morning, and the last departure from Southold is at 9:04 PM which arrives into Times Square at 11:42 PM. All services require a transfer, and take on average 2h 56m. The schedules shown below are for the next available departures.

2h 41m • 1 change

2h 41m • 1 change

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3h 3m • 1 change

2h 41m • 1 change

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3h 3m • 1 change

3h 16m • 1 change

2h 52m • 1 change

3h 14m • 1 change

2h 38m • 1 change

3h 16m • 1 change

2h 52m • 1 change

3h 14m • 1 change

2h 38m • 1 change

3h 16m • 1 change

2h 52m • 1 change

3h 14m • 1 change

2h 38m • 1 change
Want to know about travelling from Southold to Times Square? 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 Southold to Times Square. However, there are services departing from Southold station and arriving at Times Square station via Ronkonkoma. The journey, including transfers, takes approximately 2h 56m.
Southold to Times Square train services, operated by Long Island Rail Road, depart from Southold station.
Southold to Times Square train services, operated by Long Island Rail Road, arrive at New York Penn Station.
The distance between Southold and Times Square is 135.5 km. The road distance is 148 km.
You can take a train from Southold to New York Penn Station via Ronkonkoma in around 2h 53m.