Next available departures
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| Back Bay Station | Windsor Station | CheapestFastest | ||||
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| South Station (Train Terminal) | Windsor Station | No tags | ||||
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| South Station (Train Terminal) | Windsor Station | No tags | ||||
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| South Station (Train Terminal) | Windsor Station | No tags | ||||
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| South Station (Train Terminal) | Windsor Station | No tags | ||||
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| South Station (Train Terminal) | Windsor Station | No tags |
Last refresh of the prices: Today at 09:32 EDT.
Get from Boston to Windsor
The journey takes about 4 hours 3 minutes, and with fares starting at just MAD 295, it presents an excellent value for a comfortable ride.
Train Companies
Based on 6497 reviews, the company was rated 4.1 stars on Busbud. Travellers were especially satisfied with the seats and the ticket access but often complained with the Wi‑Fi. Amtrak ticket prices on this trip start at MAD 215
Frequently asked questions about travelling from Boston, MA, US to Windsor, CT, US by train
Please note that timetables, routes, or operator details shown here may be updated or vary at the time of your journey.
How much does a train ticket cost from Boston to Windsor?
The cheapest train tickets from Boston to Windsor start from MAD 295. The average price for this train route is around MAD 609. Busbud recommends booking your tickets in advance for the best chance of getting the lowest possible price.
How long is the train journey from Boston to Windsor?
The average train journey time from Boston to Windsor is 4h 3m, covering a distance of 86 miles. The fastest train gets you there in 3h 17m and is operated by Amtrak.
Which train operators serve the Boston to Windsor route?
Several major train operators run on this route with 4 trains available per day.
What are the earliest and latest departure times for the train from Boston to Windsor?
The earliest train from Boston to Windsor departs at 06:50. And the latest train departs at 15:32.
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 25 Sept 2026 with a price of MAD 323To 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 MAD 323 to MAD 2,442 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 MAD 323, which is on 2026-09-25.
