Next available departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Back Bay Station | Windsor Station | CheapestFastest | |||||
| South Station (Train Terminal) | Windsor Station | No tags | |||||
| South Station (Train Terminal) | Windsor Station | No tags | |||||
| South Station (Train Terminal) | Windsor Station | No tags | |||||
| South Station (Train Terminal) | Windsor Station | No tags | |||||
| South Station (Train Terminal) | Windsor Station | No tags | |||||
| South Station (Train Terminal) | Windsor Station | No tags | |||||
| South Station (Train Terminal) | Windsor Station | No tags |
Last refresh of the prices: Yesterday at 12:07 AM EDT.
Get from Boston to Windsor
The journey takes about 5 hours 3 minutes and with fares starting at just CLP 28,528, it presents an excellent value for a comfortable ride.
Train Companies
Based on 6445 reviews, the company was rated 4.1 stars on Busbud. Travelers were especially satisfied with the seats and the ticket access but often complained with the wifi. Amtrak ticket prices on this trip start at CLP 20,789
Frequently asked questions about traveling from Boston, MA, US to Windsor, CT, US by train
Please note that schedules, routes, or operator details shown here may be updated or vary at the time of your trip.
How much is the train ticket from Boston to Windsor?
The cheapest train tickets from Boston to Windsor start from CLP 28,528. The average price for this train route is around CLP 95,032. Busbud recommends that you book your tickets in advance for a better chance to get the lowest possible price.
How long is the train journey from Boston to Windsor?
The average train ride duration from Boston to Windsor is 5h 3m, covering a distance of 86 miles (138 km). The quickest train can get you there in 3h 17m and is operated by Amtrak.
Which train operators service the Boston to Windsor route?
Several major train operators operate on this route with 4 trains available per day.
What is the earliest and latest departure time for the train from Boston to Windsor?
The earliest train departs from Boston to Windsor at 6:50am. And the latest train departs at 3:32pm.
Find cheapest prices for trains
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from Boston, MA, US to Windsor, CT, US was searched and found on Aug 25, 2026 with a price of CLP 31,183To save money and be sure you have the best seat, it's a good idea to buy your train tickets from Boston, MA, US to Windsor, CT, US, as early as possible.
You can expect to pay from CLP 31,183 to CLP 420,493 for a train ticket from Boston, MA, US to Windsor, CT, US based on the last 2 days. You can expect to find the cheapest price for the trip at CLP 31,183 which is on 2026-08-25.
