Poughkeepsie to Windsor Trains

Poughkeepsie to Windsor trains

Travel from

Search accommodation with Expedia

Trip Overview

The average train between Poughkeepsie and Windsor takes 5h 11m and the fastest train takes 4h 39m. 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 11m
Duration: 179 mi
Distance: $63
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

$46–82

Poughkeepsie to Windsor train times

Trains run every 4 hours between Poughkeepsie and Windsor. The earliest departure is at 4:36 AM at night, and the last departure from Poughkeepsie is at 6:55 PM which arrives into Windsor at 12:06 AM. All services require a transfer at 125th Street - Harlem and take an average of 5h 11m. The schedules shown below are for the next available departures.

Departing Sunday, October 11, 2026

4:36 AM → 9:47 AM
5h 11m • 2 changes
10:58 AM → 3:53 PM
4h 55m • 2 changes
3:26 PM → 8:42 PM
5h 16m • 2 changes
5:56 PM → 11:02 PM
5h 6m • 2 changes

Departing Monday, October 12, 2026

10:48 AM → 3:45 PM
4h 57m • 2 changes
11:48 AM → 5:18 PM
5h 30m • 2 changes
3:52 PM → 8:37 PM
4h 45m • 2 changes
4:51 PM → 9:59 PM
5h 8m • 2 changes
Show more

Departing Tuesday, October 13, 2026

10:48 AM → 3:45 PM
4h 57m • 2 changes
11:48 AM → 5:18 PM
5h 30m • 2 changes
3:52 PM → 8:37 PM
4h 45m • 2 changes
4:51 PM → 9:59 PM
5h 8m • 2 changes
Show more

Departing Wednesday, October 14, 2026

10:48 AM → 3:45 PM
4h 57m • 2 changes
11:48 AM → 5:18 PM
5h 30m • 2 changes
3:52 PM → 8:37 PM
4h 45m • 2 changes
4:51 PM → 9:59 PM
5h 8m • 2 changes
Show more

Departing Thursday, October 15, 2026

10:48 AM → 3:45 PM
4h 57m • 2 changes
11:48 AM → 5:18 PM
5h 30m • 2 changes
3:52 PM → 8:37 PM
4h 45m • 2 changes
4:51 PM → 9:59 PM
5h 8m • 2 changes
Show more

Departing Friday, October 16, 2026

10:48 AM → 3:45 PM
4h 57m • 2 changes
11:48 AM → 5:18 PM
5h 30m • 2 changes
3:52 PM → 8:37 PM
4h 45m • 2 changes
4:51 PM → 9:59 PM
5h 8m • 2 changes
Show more

Departing Saturday, October 17, 2026

4:36 AM → 9:47 AM
5h 11m • 2 changes
8:58 AM → 3:53 PM
6h 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, October 11, 2026

4:36 AM → 9:47 AM

10:58 AM → 3:53 PM

3:26 PM → 8:42 PM

5:56 PM → 11:02 PM

Departing Monday, October 12, 2026

10:48 AM → 3:45 PM

11:48 AM → 5:18 PM

3:52 PM → 8:37 PM

4:51 PM → 9:59 PM

Departing Tuesday, October 13, 2026

10:48 AM → 3:45 PM

11:48 AM → 5:18 PM

3:52 PM → 8:37 PM

4:51 PM → 9:59 PM

Departing Wednesday, October 14, 2026

10:48 AM → 3:45 PM

11:48 AM → 5:18 PM

3:52 PM → 8:37 PM

4:51 PM → 9:59 PM

Departing Thursday, October 15, 2026

10:48 AM → 3:45 PM

11:48 AM → 5:18 PM

3:52 PM → 8:37 PM

4:51 PM → 9:59 PM

Departing Friday, October 16, 2026

10:48 AM → 3:45 PM

11:48 AM → 5:18 PM

3:52 PM → 8:37 PM

4:51 PM → 9:59 PM

Departing Saturday, October 17, 2026

4:36 AM → 9:47 AM

8:58 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 trips from Poughkeepsie

Train trips to Windsor

Alternative transport options