The average bus between Fenway Park and Winchester takes 1h 32m and the fastest bus takes 1h 2m. There is an hourly bus service from Fenway Park 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.
Buses run hourly between Fenway Park and Winchester. The earliest departure is at 12:02 AM at night, and the last departure from Fenway Park is at 11:17 PM which arrives into Winchester at 12:27 AM. All services require a transfer at Massachusetts Ave @ Newbury St and take an average of 1h 32m. The schedules shown below are for the next available departures.


1h 35m • 2 changes


1h 34m • 2 changes


1h 32m • 2 changes


1h 34m • 2 changes


1h 25m • 2 changes


4h 59m • 2 changes


1h 20m • 2 changes


1h 21m • 2 changes


1h 3m • 2 changes


4h 37m • 2 changes


1h 20m • 2 changes


1h 21m • 2 changes
Want to know about travelling from Fenway Park 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 bus from Fenway Park to Winchester. However, there are services departing from Fenway Park station and arriving at Winchester station via Massachusetts Ave opp Holyoke St. The journey, including transfers, takes approximately 1h 32m.
Fenway Park to Winchester bus services, operated by MBTA, depart from Massachusetts Ave @ Newbury St station.
Fenway Park to Winchester bus services, operated by MBTA, arrive at Medford Sq @ City Hall Parking lot station.
The distance between Fenway Park and Winchester is 12.2 km. The road distance is 19 km.
You can take a vehicle from Fenway Park to Laraway Rd @ Winchester Ctr via Massachusetts Ave @ Newbury St, Massachusetts Ave opp Holyoke St, Harvard, Medford Sq @ City Hall Parking lot, and 116 Riverside Ave in around 1h 56m.