New Canaan to Windsor Trains

New Canaan to Windsor trains

Travel from

Search accommodation with Expedia

Trip Overview

The average train between New Canaan and Windsor takes 3h 8m and the fastest train takes 2h 29m. The train service runs several times per day from New Canaan 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.

3h 8m
Duration: 90 mi
Distance: $44
Average price: 5 times a day
Frequency

Train via New Haven

best

Take the train from Stamford to New Haventrain New Haven
Take the train from New Haven to Windsortrain Northeast Regional / ...

3h 35m

$28–639

New Canaan to Windsor train times

Trains run 5 times a day between New Canaan and Windsor. The earliest departure is at 6:58 AM in the morning, and the last departure from New Canaan is at 8:18 PM which arrives into Windsor at 10:47 PM. All services require a transfer at Stamford and take an average of 3h 8m. The schedules shown below are for the next available departures.

Departing Friday, August 21, 2026

11:29 AM → 3:45 PM
4h 16m • 2 changes
2:29 PM → 5:18 PM
2h 49m • 2 changes
5:17 PM → 8:37 PM
3h 20m • 2 changes
8:18 PM → 10:47 PM
2h 29m • 2 changes

Departing Saturday, August 22, 2026

6:58 AM → 9:47 AM
2h 49m • 2 changes
8:57 AM → 11:53 AM
2h 56m • 2 changes
12:57 PM → 3:53 PM
2h 56m • 2 changes
2:57 PM → 5:53 PM
2h 56m • 2 changes
Show more

Departing Sunday, August 23, 2026

6:58 AM → 9:47 AM
2h 49m • 2 changes
8:57 AM → 11:53 AM
2h 56m • 2 changes
12:57 PM → 3:53 PM
2h 56m • 2 changes
2:57 PM → 5:53 PM
2h 56m • 2 changes
Show more

Departing Monday, August 24, 2026

11:29 AM → 3:45 PM
4h 16m • 2 changes
2:29 PM → 5:18 PM
2h 49m • 2 changes
5:17 PM → 8:37 PM
3h 20m • 2 changes
8:18 PM → 10:47 PM
2h 29m • 2 changes

Departing Tuesday, August 25, 2026

11:29 AM → 3:45 PM
4h 16m • 2 changes
2:29 PM → 5:18 PM
2h 49m • 2 changes
5:17 PM → 8:37 PM
3h 20m • 2 changes
8:18 PM → 10:47 PM
2h 29m • 2 changes

Departing Wednesday, August 26, 2026

11:29 AM → 3:45 PM
4h 16m • 2 changes
2:29 PM → 5:18 PM
2h 49m • 2 changes
5:17 PM → 8:37 PM
3h 20m • 2 changes
8:18 PM → 10:47 PM
2h 29m • 2 changes

Departing Thursday, August 27, 2026

11:29 AM → 3:45 PM
4h 16m • 2 changes
2:29 PM → 5:18 PM
2h 49m • 2 changes
5:17 PM → 8:37 PM
3h 20m • 2 changes
8:18 PM → 10:47 PM
2h 29m • 2 changes

Frequently asked questions

Want to know about travelling from New Canaan 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.