There are 4 ways to get from Poughkeepsie to Windsor by train (Amtrak), bus (Greyhound), car, train, or bus
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Train
best- Take the train from Poughkeepsie to 125th Street - Harlemtrain
- Take the train from 125th Street - Harlem to New Haventrain
- Take the train from New Haven to Windsortrain
5h 48m$47–86Drive 81.6 mi
cheapest- Drive from Poughkeepsie to Windsorcar 81.6 mi
2h 9m$15–22Bus
- Take the bus from Metro North Station to TransCenterbus Wpp
- Take the bus from White Plains Bus Station to Hartford Union Stationbus Greyhound US0240
6h 8m$18–38Train, bus
- Take the train from Poughkeepsie to New York Penn Stationtrain VIA Rail
- Take the bus from New York to Hartfordbus Ppb 5623 / ...
6h 25m$43–200
Poughkeepsie to Windsor by train
Comparing Your Travel Options
The cheapest way to get from Poughkeepsie to Windsor is to drive which costs $14 - $22 and takes 2h 9m.
The fastest way to get from Poughkeepsie to Windsor is to drive which takes 2h 9m and costs $14 - $22.
No, there is no direct bus from Poughkeepsie station to Windsor. However, there are services departing from Metro North Station and arriving at Central St @ Broad St via White Plains Bus Station, Hartford Union Station and Central Row South Side @ Travelers. The journey, including transfers, takes approximately 6h 8m.
No, there is no direct train from Poughkeepsie to Windsor. However, there are services departing from Poughkeepsie and arriving at Windsor via 125th Street - Harlem and New Haven. The journey, including transfers, takes approximately 5h 48m.
The distance between Poughkeepsie and Windsor is 181 miles. The road distance is 82.1 miles.
The best way to get from Poughkeepsie to Windsor without a car is to train which takes 5h 48m and costs $45 - $90.
It takes approximately 5h 48m to get from Poughkeepsie to Windsor, including transfers.
Poughkeepsie to Windsor bus services, operated by Leprechaun Lines, depart from Metro North Station.
Poughkeepsie to Windsor train services, operated by Metro-North Railroad (MNR), depart from Poughkeepsie station.
The best way to get from Poughkeepsie to Windsor is to train which takes 5h 48m and costs $45 - $90. Alternatively, you can bus, which costs $18 - $40 and takes 6h 8m.
What companies run services between Poughkeepsie, NY, USA and Windsor, CT, USA?
You can take a train from Poughkeepsie to Windsor via 125th Street - Harlem and New Haven in around 5h 48m. Alternatively, you can take a bus from Metro North Station to Central St @ Broad St via TransCenter, White Plains Bus Station, Hartford Union Station, and Central Row South Side @ Travelers in around 6h 8m.
- Phone
- +1 877.690.5114
- Website
- Metro North Railroad
Train from Poughkeepsie to 125th Street - Harlem
- Ave. Duration
- 1h 39m
- Frequency
- Hourly
- Estimated price
- $18–28
- Website
- Metro North Railroad
- Schedules at
- Metro North Railroad Schedules
- Off-Peak
- $18–21
- Peak
- $25–28
Train from 125th Street - Harlem to New Haven
- Ave. Duration
- 1h 59m
- Frequency
- Every 30 minutes
- Estimated price
- $18–28
- Website
- Metro North Railroad
- Schedules at
- Metro North Railroad Schedules
- Off-Peak
- $18–21
- Peak
- $25–28
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from New Haven to Windsor
- Ave. Duration
- 53 min
- Frequency
- Every 4 hours
- Estimated price
- $11–30
- Website
- Amtrak
- Phone
- +1 888 842-7245
- Website
- VIA Rail
Train from Poughkeepsie to New York Penn Station
- Ave. Duration
- 1h 40m
- Frequency
- Once daily
- Estimated price
- $19–160
- Website
- VIA Rail
- Escape
- $19–70
- Business
- $50–150
- Business Plus
- $60–160
- Economy
- $21–75
- Economy Plus
- $23–80
- Phone
- +1 800-624-4217
- [email protected]
- Website
- Leprechaun Lines
Bus from Metro North Station to TransCenter
- Ave. Duration
- 1h 46m
- Frequency
- 4 times a day
- Estimated price
- $1–9
- Schedules at
- Leprechaun Lines
- Newburgh - Beacon Shuttle
- $1
- Newburgh Local
- $2
- White Plains Commuter
- $7–9
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from White Plains Bus Station to Hartford Union Station
- Ave. Duration
- 2h 25m
- Frequency
- Once daily
- Estimated price
- $15–24
- Website
- Greyhound
- Phone
- 1-800-343-9999
- Website
- Peter Pan
Bus from New York to Hartford
- Ave. Duration
- 2h 35m
- Frequency
- Every 2 hours
- Estimated price
- $22–40
- Website
- Peter Pan
Want to know more about travelling around United States
Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.
Related travel guides
Travelling to the US: What do I need to know?
Read the travel guide
Why you should take the train in the US
Read the travel guide
Italian Lakes: Getting around by train
Read the travel guide
Booking & Getting There
Poughkeepsie to Windsor bus services, operated by Leprechaun Lines, arrive at TransCenter station.
Poughkeepsie to Windsor train services, operated by Metro-North Railroad (MNR), arrive at 125th Street - Harlem station.
Yes, the driving distance between Poughkeepsie to Windsor is 82 miles. It takes approximately 2h 9m to drive from Poughkeepsie to Windsor.
Book your Poughkeepsie to Windsor train tickets online with Omio.
There are 182+ hotels available in Windsor.
















