Poughkeepsie to Windsor Trains

Poughkeepsie to Windsor trains

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Trip Overview

The average train between Poughkeepsie and Windsor takes 5h 17m and the fastest train takes 4h 27m. The train service runs several times per day from Poughkeepsie 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.

5h 17m
Duration: 179 mi
Distance: $78
Average price: Every 4 hours
Frequency

Train

best

Take the train from Poughkeepsie to 125th Street - Harlemtrain
Take the train from 125th Street - Harlem to New Haventrain
Take the train from New Haven to Windsortrain

5h 48m

$59–96

Poughkeepsie to Windsor train times

Trains run every 4 hours between Poughkeepsie and Windsor. The earliest departure is at 5:58 AM in the morning, and the last departure from Poughkeepsie is at 8:49 PM which arrives into Windsor at 9:47 AM. All services require a transfer at 125th Street - Harlem and take an average of 5h 17m. The schedules shown below are for the next available departures.

Departing Sunday, November 1, 2026

5:58 AM → 11:53 AM
5h 55m • 2 changes
10:58 AM → 3:53 PM
4h 55m • 2 changes
12:51 PM → 5:53 PM
5h 2m • 2 changes
2:55 PM → 7:34 PM
4h 39m • 2 changes
Show more

Departing Monday, November 2, 2026

6:08 AM → 10:35 AM
4h 27m • 2 changes
6:44 AM → 11:49 AM
5h 5m • 2 changes
10:48 AM → 3:45 PM
4h 57m • 2 changes
11:48 AM → 5:18 PM
5h 30m • 2 changes
Show more

Departing Tuesday, November 3, 2026

6:08 AM → 10:35 AM
4h 27m • 2 changes
6:44 AM → 11:49 AM
5h 5m • 2 changes
10:48 AM → 3:45 PM
4h 57m • 2 changes
11:48 AM → 5:18 PM
5h 30m • 2 changes
Show more

Departing Wednesday, November 4, 2026

6:08 AM → 10:35 AM
4h 27m • 2 changes
6:44 AM → 11:49 AM
5h 5m • 2 changes
10:48 AM → 3:45 PM
4h 57m • 2 changes
11:48 AM → 5:18 PM
5h 30m • 2 changes
Show more

Departing Thursday, November 5, 2026

6:08 AM → 10:35 AM
4h 27m • 2 changes
6:44 AM → 11:49 AM
5h 5m • 2 changes
10:48 AM → 3:45 PM
4h 57m • 2 changes
11:48 AM → 5:18 PM
5h 30m • 2 changes
Show more

Departing Friday, November 6, 2026

6:08 AM → 10:35 AM
4h 27m • 2 changes
6:44 AM → 11:49 AM
5h 5m • 2 changes
10:48 AM → 3:45 PM
4h 57m • 2 changes
11:48 AM → 5:18 PM
5h 30m • 2 changes
Show more

Departing Saturday, November 7, 2026

5:58 AM → 11:53 AM
5h 55m • 2 changes
10:58 AM → 3:53 PM
4h 55m • 2 changes
12:51 PM → 5:53 PM
5h 2m • 2 changes
2:55 PM → 7:34 PM
4h 39m • 2 changes
Show more

Frequently asked questions

Want to know about travelling from Poughkeepsie 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.

Poughkeepsie to Windsor trains

Find Transport to Windsor

Trip Overview

Train

Poughkeepsie to Windsor train times

Departing Sunday, November 1, 2026

5:58 AM → 11:53 AM

10:58 AM → 3:53 PM

12:51 PM → 5:53 PM

2:55 PM → 7:34 PM

Departing Monday, November 2, 2026

6:08 AM → 10:35 AM

6:44 AM → 11:49 AM

10:48 AM → 3:45 PM

11:48 AM → 5:18 PM

Departing Tuesday, November 3, 2026

6:08 AM → 10:35 AM

6:44 AM → 11:49 AM

10:48 AM → 3:45 PM

11:48 AM → 5:18 PM

Departing Wednesday, November 4, 2026

6:08 AM → 10:35 AM

6:44 AM → 11:49 AM

10:48 AM → 3:45 PM

11:48 AM → 5:18 PM

Departing Thursday, November 5, 2026

6:08 AM → 10:35 AM

6:44 AM → 11:49 AM

10:48 AM → 3:45 PM

11:48 AM → 5:18 PM

Departing Friday, November 6, 2026

6:08 AM → 10:35 AM

6:44 AM → 11:49 AM

10:48 AM → 3:45 PM

11:48 AM → 5:18 PM

Departing Saturday, November 7, 2026

5:58 AM → 11:53 AM

10:58 AM → 3:53 PM

12:51 PM → 5:53 PM

2:55 PM → 7:34 PM

Frequently asked questions

What companies run services between Poughkeepsie, NY, USA and Windsor, CT, USA?

Train from Poughkeepsie to 125th Street - Harlem

Train from 125th Street - Harlem to New Haven

Train from New Haven to Windsor

Train trips from Poughkeepsie

Train trips to Windsor

Alternative transport options