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Trip Summary
You can pick from 2 daily train trips between Windsor and Middletown. The average train journey from Windsor to Middletown takes 7 hours and 45 minutes, but some Amtrak train trips are as short as 6 hours and 49 minutes.
| Distance | 242 mi (389 km) |
| Fastest train | 6h 49m |
| Lowest price | $177.07 |
| Most frequent service | Amtrak |
| Train lines | 1 |
Which train should you take from Windsor to Middletown?
Amtrak is the one and only train line which connects Windsor to Middletown. The schedule is relatively limited as the train only runs twice a day.
| Train | Daily Trips | Avg. Time | Avg. Price |
|---|---|---|---|
| Amtrak | 2 | 7h 46m | $224.24 |
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 Windsor to Middletown every day, as well as 2 trips on the weekends, with prices starting from $177.
Frequently Asked Questions
The distance between Windsor and Middletown is approximately 242 miles, or 389 kilometers. The average train journey between these two cities takes 7 hours and 45 minutes, although the absolute fastest you could get there is 6 hours and 49 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 departing from Windsor to Middletown tend to have the most passengers on Monday. With higher demand ticket prices also tend to be higher on Monday. If you are trying to snag a cheap train tickets or just want an emptier train you'll have better luck by booking travel departing on Thursday as the least number of people tend to travel then.
The earliest train departs Windsor at 7:00am while the last train of the day leaves at 8:00am. 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 Windsor 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 Middletown to Windsor.
City Information
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.
Middletown
Image credit: Unsplash
Middletown is a very common place name in Pennsylvania, but the most significant is the borough of Middletown just south of Harrisburg. Though Middletown itself is pretty small, the Harrisburg International Airport is within Middletown and brings a good amount of traffic through the town. However, the area's charming activities and landscape merit a few days of slowing down and enjoying central Pennsylvania.
Families with young kids will love wandering through the enormous National Christmas Center, open during Christmas Season and for select weeks in July, filled with holiday displays, decor, and gifts. You can enter the spooky, spiky Indian Echo Caverns in nearby Derry Township to discover local natural history or enjoy nature's fresh air on the Swatara Creek Water Trail and the Jonathan Eshenour Memorial Trail.
Middletown is home to several brewing companies, distilleries, and brewpubs, including the famous Appalachian Brewing Company and Tattered Flag. In Downtown Middletown, you can shop at a handful of malls and enjoy entertainment at hotels, clubs, bars, and museums.
No intercity bus companies stop in Middletown, but Amtrak's Keystone Service provides train service to the station downtown. Catch the train west to Harrisburg or as far east as Philadelphia.
Station Information
Where is the train station in Windsor?
Main departure station: 41 Central St
There is one train station in Windsor.
All train stations in Windsor:
41 Central St
Where is the train station in Middletown?
Main arrival station: 270 West Emaus Street
Middletown has one train station.
Train stations in Middletown:
270 West Emaus Street
Get around town with Moovit
Need a return trip from Middletown to Windsor?
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