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Pittsfield to Windsor trains

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Trip Overview

The average train between Pittsfield and Windsor takes 4h 17m and the fastest train takes 2h 34m. There is at least one train per day from Pittsfield to Windsor. The journey time may be longer on weekends and holidays; use the search form on this page to search for a specific travel date.

4h 17m
Duration
71 mi
Distance
$46
Average price
Once daily
Frequency

Pittsfield to Windsor train times

Trains run once daily between Pittsfield and Windsor. The service departs Pittsfield at 4:30 PM in the afternoon, which arrives into Windsor at 19:04:00. All services require a transfer, and take on average 4h 17m. The schedules shown below are for the next available departures.

Departing Wednesday, November 11, 2026

  •  → 

    AmtrakAmtrak2h 34m • 1 change

Departing Thursday, November 12, 2026

  •  → 

    AmtrakAmtrak2h 34m • 1 change

Departing Friday, November 13, 2026

  •  → 

    AmtrakAmtrak2h 34m • 1 change

Departing Saturday, November 14, 2026

  •  → 

    Arrives next day

    AmtrakAmtrak13h 44m • 1 change

Departing Sunday, November 15, 2026

  •  → 

    AmtrakAmtrak3h 26m • 1 change

Departing Monday, November 16, 2026

  •  → 

    AmtrakAmtrak2h 34m • 1 change

Departing Tuesday, November 17, 2026

  •  → 

    AmtrakAmtrak2h 34m • 1 change

Frequently asked questions

Want to know about travelling from Pittsfield to Windsor? 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.

Map of how to get from Pittsfield to Windsor.ExpandLaunch map view
  • Distance: 70.8 mi
  • Duration: 4h 17m

What companies run services between Pittsfield, MA, USA and Windsor, CT, USA?

You can take a train from Pittsfield Amtrak Station to Windsor via Springfield in around 2h 44m.

Operators