The average train between Wellesley and Winchester takes 1h 47m and the fastest train takes 1h 9m. There is a train service every few hours from Wellesley to Winchester. 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 hourly between Wellesley and Winchester. The earliest departure is at 12:19 AM at night, and the last departure from Wellesley is at 11:44 PM which arrives into Winchester at 5:36 AM. All services require a transfer at Back Bay and take an average of 1h 47m. The schedules shown below are for the next available departures.


2h 32m • 2 changes


2h 32m • 2 changes


2h 30m • 2 changes


2h 30m • 2 changes


6h 17m • 2 changes


2h 32m • 2 changes


2h 32m • 2 changes


2h 30m • 2 changes


5h 17m • 2 changes


1h 32m • 2 changes


1h 22m • 2 changes


1h 45m • 2 changes


1h 32m • 2 changes


1h 22m • 2 changes


1h 45m • 2 changes


1h 58m • 2 changes
Want to know about travelling from Wellesley to Winchester? 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 Wellesley to Winchester. However, there are services departing from Wellesley station and arriving at Winchester station via Back Bay. The journey, including transfers, takes approximately 1h 47m.
Wellesley to Winchester train services, operated by MBTA, depart from Wellesley Square station.
Wellesley to Winchester train services, operated by MBTA, arrive at Winchester Center station.
The distance between Wellesley and Winchester is 21.5 km. The road distance is 38 km.
You can take a train from Wellesley Square to Winchester Center via Back Bay, Back Bay, North Station, and North Station in around 1h 40m.