Cheap train tickets from Windsor, CT to Brattleboro, VT
Find and compare the best ground travel options in one place.
Trip Summary
There is one daily train from Windsor, CT to Brattleboro, VT. Traveling by train from Windsor, CT to Brattleboro, VT usually takes 5 hours and 3 minutes, but the fastest Amtrak train can make the trip in 5 hours.
- Distance
- 69 mi (111 km)
- Fastest train
- 5h
- Lowest price
- $30.00
- Trains per day
- 1
- Most frequent service
- Amtrak
- Train lines
- 1
Millions of travelers trust Wanderu every year to get:
Lowest Prices
We find the cheapest bus & train tickets, so you can wander for less.
Best Travel Options
We partner with 500+ carriers to bring you the most bus & train options.
Quick & Easy Booking
Book trips quickly with a simple, hassle-free checkout – online & on our app.
Fast Customer Support
We don’t monkey around. We respond within minutes to help you out.
See what travelers are saying about Wanderu:
Windsor, CT to Brattleboro, VT Train Schedule

Train Trip Reviews from Wanderu Customers
Average score for trains from Windsor, CT to Brattleboro, VT (Based on 1 rating and review)
5.0
There are several train options that can take you from Windsor, CT to Brattleboro, VT:
See more detailsWhat is the price of a train ticket from Windsor, CT to Brattleboro, VT?
In the last month, train tickets from Windsor, CT to Brattleboro, VT cost about $31 when booked at the cheapest time. Compared to most train fares, this is an excellent price. Good news! You can find the cheapest tickets if you book your trip at least 19 days prior to the travel date. You’ll likely pay around $0.50 more if you wait to book until the last minute.
Average train ticket prices from Windsor, CT to Brattleboro, VT by travel date
The cost of a one-way train trip from Windsor, CT to Brattleboro, VT is expected to stay pretty stable over the next four weeks. No matter which day you travel, you can expect to pay about $30 for your ticket.
Prices as travel date approaches
Which train should you take from Windsor, CT to Brattleboro, VT?
Amtrak is the one and only train line which connects Windsor, CT to Brattleboro, VT. Furthermore, there is only one train per day, so you will have to plan your travel around this limited availability. On the other hand, you won't have to spend a ton of time comparing a bunch of possible options.
| Train | Daily Trips | Avg. Time | Avg. Price |
|---|---|---|---|
| Amtrak | 1 | 5h 3m | $30.91 |
Amtrak is the largest passenger railroad service in America, offering daily intercity trains to hundreds of destinations across the contiguous United States, as well as several cities in Canada. Every Amtrak train comes equipped with comfortable seats with extra legroom, as well as several four-seat areas with tables in the middle. In addition, each car has a freshly cleaned restroom, free WiFi and power outlets at every seat. There are also snack bars where you can purchase drinks or food during your journey. On average, there is 1 Amtrak train from Windsor, CT to Brattleboro, VT every day, as well as 1 trip on the weekends, with prices starting from $30.










Frequently asked questions about traveling by train from Windsor, CT to Brattleboro, VT
Typically there is only one scheduled train per day. However, it is not a direct train. This means that you will need to disembark from your original train and board a connecting train at some point during your journey. You will need to remember to bring your carry-on luggage with you when you transfer trains. Depending on the carrier's policy, you may also be responsible for transferring your own checked baggage. You can also take a train for your return trip from Brattleboro, VT to Windsor, CT.
Trains per day
1
Direct trains
0
The distance between Windsor, CT and Brattleboro, VT is approximately 69 miles. The average train journey between these two cities takes 5 hours and 3 minutes, although the absolute fastest you could get there is 5 hours. Looking for ways to pass the time? Most trains are equipped with Wi-Fi, which means you can stream music, browse social media or get some work done during your ride. That said, in case your train has a spotty signal, or is among the few without Wi-Fi, we also recommend downloading TV shows and movies to your mobile device in advance of your trip. That way the ride will fly by whatever the Wi-Fi situation.
Distance (mi)
69
Distance (km)
111
Most days, there is only one train which leaves Windsor, CT at 11:49 AM and arrives in Brattleboro, VT around 5 hours later.
First train
11:49am
Last train
11:53am
Trains from Windsor, CT to Brattleboro, VT are the most crowded on Sunday. Tickets also tend to be more expensive then. If you are looking for a great deal on your train tickets or just want extra room to stretch out, consider traveling on Monday instead, as it tends to be the least crowded day of the week.
Busiest
Sunday
Least crowded
Monday
City Information
Windsor

Outside of Hartford is Windsor, a charming Connecticut town that is known as the state's first English settlement. Due to this, the city has several historical sites and antique museums, like the Windsor Historical Society, The New England Air Museum, and Oliver Ellsworth Homestead, with pieces dating back to the 1700s. Outdoor enthusiasts will be pleased with the town's many parks and green spaces, from Northwest Park to the Windsor Center River Trail.
Visit Windsor just after a snowfall with your snowshoes or cross-country skis, and explore the beautiful Northwest Park. Hartford is only six minutes by train from Windsor, offering a weekend of fun and nightlife. Beer lovers can visit the iconic Back East Brewery and Thomas Hooker Brewery, while the Northwest Park Country Fair features competitions, live music, auctions, performances, and more. If you enjoy golf, check out the Keney Park Golf Course, dating back to 1927.
Windsor offers great transport links to and from other cities, especially when you're moving by train. Over 100 cities have train links through Amtrak, while a few buses also serve the town. Within Windsor, the CT-transit Hartford provides local bus service.
Station Information
Where is the train station in Windsor, CT?
Main departure station: 41 Central St
There is one train station in Windsor, CT.
All train stations in Windsor, CT:
- 41 Central St
Where is the train station in Brattleboro, VT?
Main arrival station: Brattleboro, Vermont
Brattleboro, VT has one train station.
All train stations in Brattleboro, VT:
- Brattleboro, Vermont
Need a return trip from Brattleboro, VT to Windsor, CT?
Search Train Tickets
Wanderu is the simplest way to book bus and train travel.
With just a quick search on Wanderu, you can compare bus and train schedules and prices from hundreds of travel companies in one convenient place to find the trip that works best for you. Wanderu’s simple checkout process makes it easy to book cheap bus and train tickets hassle-free. Most importantly, as Wanderu is an official partner of all leading bus and train companies, we always have the best bus and train deals out there.




