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Trip Summary
There is usually just one train option from Pittsfield to Windsor per day. The average train journey from Pittsfield to Windsor takes 3 hours and 32 minutes, but some Amtrak train trips are as short as 3 hours and 26 minutes.
| Distance | 52 mi (83 km) |
| Fastest train | 3h 26m |
| Lowest price | $21.00 |
| Most frequent service | Amtrak |
| Train lines | 1 |
What is the price of a train ticket from Pittsfield to Windsor?
In the last month, the average price of a train ticket from Pittsfield to Windsor was $21.00. This is basically as cheap as train fares can get. Good news! You can find the cheapest tickets if you book your trip at least 20 days prior to the travel date. You’ll likely pay around $8.00 more if you wait to book until the last minute.
Monthly average prices
Which train should you take from Pittsfield to Windsor?
Amtrak is the one and only train line which connects Pittsfield to Windsor. 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 | 3h 33m | $26.82 |
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 1 Amtrak trains from Pittsfield to Windsor every day, as well as 1 trips on the weekends, with prices starting from $18.
Frequently Asked Questions
The distance between Pittsfield and Windsor is approximately 52 miles, or 83 kilometers. The average train journey between these two cities takes 3 hours and 32 minutes, although the absolute fastest you could get there is 3 hours and 26 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.
On a weekly basis, the greatest number of passengers tend to travel by trains from Pittsfield to Windsor on Saturday. Tickets for Saturday tend to also be the most expensive. For savvy travelers looking for cheaper priced tickets search for travel departing on Friday. Friday also tend to have less passengers which may make boarding faster and let you snag your perfect seat.
Most days, there is only one train which leaves Pittsfield at 4:00pm and arrives in Windsor around 3 hours later.
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 Windsor to Pittsfield.
City Information
Pittsfield
Image credit: Unsplash
Pittsfield is the largest city in the Berkshires region, Massachusetts. It is famous for having iconic residents like the author of Moby Dick, Herman Melville, and Rev. Thomas Allen of the Revolutionary War. Pittsfield offers many outdoor activities, like hiking on the Ashuwillticook Rail Trail or skiing on a 750-foot mountain at Bousquet Mountain Ski Area. Campers can check out the Pittsfield State Forest, while Lake Onota offers a scenic view. There are also different areas for history in Pittsfield, like the Hancock Shaker Village, which features living history exhibits, and the Berkshire Museum offers natural history. The city is popular among young families due to its fun activities and green spaces.
Pittsfield's downtown is the cultural center of Massachusetts, boasting an exciting dining scene with bars, cafés, and live music. Local stores also look out for when shopping and fun events like the Pittsfield Photo Challenge and the Berkshire International Film Festival. The latest addition is the Stargaze LGBTQ+ Festival in August.
Six bus routes go to Pittsfield, all powered by Greyhound. There are plenty of train services as well, offered by Amtrak and Amtrak Lake Shore Limited. Within the city, the Berkshire Regional Transit Authority provides public transportation.
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 Pittsfield?
Main departure station: Scelsi Transp Ctr - 1 Columbus Ave
There is one train station in Pittsfield.
All train stations in Pittsfield:
Scelsi Transp Ctr - 1 Columbus Ave
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
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