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.
Trip Summary
There are usually 2 daily train trips available from Poughkeepsie to Windsor. Traveling by train from Poughkeepsie to Windsor usually takes 6 hours and 1 minute, but the fastest Amtrak train can make the trip in 5 hours and 17 minutes.
| Distance | 67 mi (107 km) |
| Fastest train | 5h 17m |
| Lowest price | $54.00 |
| Most frequent service | Amtrak |
| Train lines | 1 |
Which train should you take from Poughkeepsie to Windsor?
Amtrak is the one and only train line which connects Poughkeepsie to Windsor. The schedule is relatively limited as the train only runs twice a day.
| Train | Daily Trips | Avg. Time | Avg. Price |
|---|---|---|---|
| Amtrak | 2 | 6h 1m | $106.66 |
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 are 2 Amtrak trains from Poughkeepsie to Windsor every day, as well as 2 trips on the weekends, with prices starting from $54.
Frequently Asked Questions
The distance between Poughkeepsie and Windsor is approximately 67 miles, or 107 kilometers. The average train journey between these two cities takes 6 hours and 1 minute, although the absolute fastest you could get there is 5 hours and 17 minutes.
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.
Trains from Poughkeepsie to Windsor are the most crowded on Monday. 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 Wednesday instead, as it tends to be the least crowded day of the week.
The earliest train departs Poughkeepsie at 11:00am while the last train of the day leaves at 4:00pm. To see all scheduled departure times, use the search function on this page to get the full schedule for your specific travel dates.
Trains leave the station in Poughkeepsie twice a day, so there are a couple of options depending on your preferred travel time. However, there are no direct trains. 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 change 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 Windsor to Poughkeepsie.
City Information
Poughkeepsie
Poughkeepsie is nicknamed the second capital of New York for a good reason – the bustling city has breathtaking views of the Hudson River and is a quick weekend destination for New Yorkers. Art buffs can visit the Barrett Art Center and Frances Lehman Loeb Art Center, while history lovers will enjoy the National Register of Historic Places. Poughkeepsie is a true university town with campuses for the Culinary Institute of America, Vassar College, and Marist College. If music is your thing, you can check what's playing at the iconic Barvadon Opera House. The city is also an excellent place for picnics and outdoor activities, especially on the riverfront.
Poughkeepsie is known for its wide range of restaurants, ranging from farm-to-table establishments to breweries and brewpubs. The craft beer scene is upcoming, with beer gardens and pubs to check out. Nightlife keeps the fun going with comedy clubs, champagne bars, and lounges.
Poughkeepsie is easily accessible via Amtrak. The Amtrak Lake Shore Limited, Maple Leaf, Empire Service, and Ethan Allen Express stop in Poughkeepsie en route to New York City, Philadelphia, Rensselaer, Newark, and other cities. The central and busiest station is 41 Main St, and many other trains make stops in and around Poughkeepsie. Poughkeepsie is also accessible by Greyhound buses. Most visitors and locals use the Newburgh Airport, only about 15 miles away, for air travel.
Windsor
Image credit: Unsplash
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 Poughkeepsie?
Main departure station: 41 Main St
There is one train station in Poughkeepsie.
All train stations in Poughkeepsie:
41 Main St
Where is the train station in Windsor?
Main arrival station: 41 Central St
Windsor has one train station.
All train stations in Windsor:
41 Central St
Get around town with Moovit
Need a return trip from Windsor to Poughkeepsie?
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.
Book buses and trains on the go with the Wanderu app.
Download our app and snag the best travel deals across North America & Europe.Learn more