There are 11 ways to get from Windsor to Milford by plane, train, bus, car, or bus (Greyhound)
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly to Laguardia Airport, train
best- Fly from Detroit (DTW) to Laguardia Airport (LGA)plane DTW - LGA
- Take the train from 125th Street - Harlem to Milfordtrain
6h 19m$171–486Fly to Westchester County Airport, line 971 bus, train
cheapest- Fly from Detroit (DTW) to Westchester County Airport (HPN)plane DTW - HPN
- Take the bus from Main St @ South Broadway to Stamford Transportation Center @ Bay Abus
- Take the train from Stamford to Milfordtrain
7h 29m$116–676Bus, train
- Take the bus from Detroit Bus Station to Toledo Bus Stopbus
- Take the bus from Toledo Bus Stop to New York Midtownbus
- Take the train from Grand Central Terminal to Milfordtrain
16h 39m$121–222Train
- Take the train from Windsor to Aldershottrain
- Take the train from Aldershot to Yonkerstrain
- Take the train from 125th Street - Harlem to Milfordtrain
18h 42m$202–530Drive 640.4 mi
- Drive from Windsor to Milfordcar 640.4 mi
12h 8m$147–212Fly to John F. Kennedy International Airport, train
- Fly from Detroit (DTW) to John F. Kennedy International Airport (JFK)plane DTW - JFK
- Take the train from Grand Central Terminal to Milfordtrain
6h 27m$353–997Fly to Bradley International Airport, train
- Fly from Detroit (DTW) to Bradley International Airport (BDL)plane DTW - BDL
- Take the train from Windsor Locks to New Haventrain
6h 40m$120–694Fly to Newark Liberty International Airport, train
- Fly from Detroit (DTW) to Newark Liberty International Airport (EWR)plane DTW - EWR
- Take the train from Newark Liberty International Airport to Bridgeport Amtrak Stationtrain
7h 16m$195–1,158Bus, train via Springfield
- Take the bus from Detroit Bus Station to Toledo Bus Stopbus
- Take the train from Toledo to Springfieldtrain
- Take the train from Springfield to New Haventrain
19h 15m$187–488Bus, train via Stamford
- Take the bus from Detroit Bus Station to Toledo Bus Stopbus
- Take the train from Toledo to Ny Moynihan Train Hall At Penn Stationtrain
- Take the train from Ny Moynihan Train Hall At Penn Station to Stamford Amtrak Stationtrain
- Take the train from Stamford to Milfordtrain
19h 54m$194–1,024Bus
- Take the bus from Detroit Bus Station to Port Authority Bus Terminalbus Greyhound US0420
- Take the bus from New York to New Havenbus Bz 0210
20h 30m$134–213
Windsor to Milford by bus, foot, and train
Comparing Your Travel Options
The cheapest way to get from Windsor to Milford is to bus and train which costs $120 - $230 and takes 16h 39m.
The fastest way to get from Windsor to Milford is to fly and train which takes 6h 19m and costs $170 - $490.
No, there is no direct bus from Windsor station to Milford. However, there are services departing from Detroit Bus Station and arriving at New Haven via New York. The journey, including transfers, takes approximately 20h 30m.
No, there is no direct train from Windsor to Milford. However, there are services departing from Windsor and arriving at Milford via Aldershot, Yonkers and 125th Street - Harlem. The journey, including transfers, takes approximately 18h 42m.
The distance between Windsor and Milford is 592 miles. The road distance is 644.1 miles.
The best way to get from Windsor to Milford without a car is to bus and train which takes 16h 39m and costs $120 - $230.
It takes approximately 6h 19m to get from Windsor to Milford, including transfers.
Windsor to Milford bus services, operated by Greyhound USA, depart from Detroit Bus Station.
Windsor to Milford train services, operated by VIA Rail, depart from Windsor station.
The best way to get from Windsor to Milford is to train which takes 18h 42m and costs $200 - $550. Alternatively, you can bus, which costs $130 - $220 and takes 20h 30m.
What companies run services between Windsor, ON, Canada and Milford, CT, USA?
You can take a train from Windsor to Milford via Aldershot, Yonkers, and 125th Street - Harlem in around 18h 42m. Alternatively, you can take a bus from Detroit Bus Station to Milford via Port Authority Bus Terminal, New York, New Haven, and New Haven in around 20h 30m.
- Website
- delta.com
Flights from Detroit to Laguardia Airport
- Ave. Duration
- 1h 49m
- When
- Every day
- Estimated price
- $110–700
Flights from Detroit to Laguardia Airport via Rochester
- Ave. Duration
- 3h 31m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $110–700
Flights from Detroit to Laguardia Airport via Pittsburgh
- Ave. Duration
- 3h 44m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $110–700
Flights from Detroit to Laguardia Airport via Cleveland
- Ave. Duration
- 3h 50m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $110–700
Flights from Detroit to John F. Kennedy International Airport
- Ave. Duration
- 1h 55m
- When
- Every day
- Estimated price
- $65–380
Flights from Detroit to John F. Kennedy International Airport via Rochester
- Ave. Duration
- 4h 21m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $65–400
Flights from Detroit to Bradley International Airport
- Ave. Duration
- 1h 42m
- When
- Every day
- Estimated price
- $100–650
Flights from Detroit to Newark Liberty International Airport
- Ave. Duration
- 1h 43m
- When
- Every day
- Estimated price
- $65–400
Flights from Detroit to Westchester County Airport
- Ave. Duration
- 1h 44m
- When
- Every day
- Estimated price
- $100–650
- Phone
- +1 877.690.5114
- Website
- Metro North Railroad
Train from 125th Street - Harlem to Milford
- Ave. Duration
- 1h 34m
- Frequency
- Every 30 minutes
- Estimated price
- $16–26
- Website
- Metro North Railroad
- Schedules at
- Metro North Railroad Schedules
- Off-Peak
- $16–19
- Peak
- $22–26
Train from Grand Central Terminal to Milford
- Ave. Duration
- 1h 44m
- Frequency
- Every 30 minutes
- Estimated price
- $17–27
- Website
- Metro North Railroad
- Schedules at
- Metro North Railroad Schedules
- Off-Peak
- $17–20
- Peak
- $24–27
Train from 125th Street - Harlem to Milford
- Ave. Duration
- 1h 34m
- Frequency
- Every 30 minutes
- Estimated price
- $16–26
- Website
- Metro North Railroad
- Schedules at
- Metro North Railroad Schedules
- Off-Peak
- $16–19
- Peak
- $22–26
Train from Grand Central Terminal to Milford
- Ave. Duration
- 1h 44m
- Frequency
- Every 30 minutes
- Estimated price
- $17–27
- Website
- Metro North Railroad
- Schedules at
- Metro North Railroad Schedules
- Off-Peak
- $17–20
- Peak
- $24–27
Train from Stamford to Milford
- Ave. Duration
- 55 min
- Frequency
- Every 30 minutes
- Estimated price
- $10–17
- Website
- Metro North Railroad
- Schedules at
- Metro North Railroad Schedules
- Off-Peak
- $10–13
- Peak
- $15–17
Train from Stamford to Milford
- Ave. Duration
- 55 min
- Frequency
- Every 30 minutes
- Estimated price
- $10–17
- Website
- Metro North Railroad
- Schedules at
- Metro North Railroad Schedules
- Off-Peak
- $10–13
- Peak
- $15–17
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Detroit Bus Station to Toledo Bus Stop
- Ave. Duration
- 1h 5m
- Frequency
- Every 4 hours
- Estimated price
- $9–15
- Website
- Greyhound
Bus from Detroit Bus Station to Toledo Bus Stop
- Ave. Duration
- 1h 5m
- Frequency
- Every 4 hours
- Estimated price
- $9–15
- Website
- Greyhound
Bus from Detroit Bus Station to Toledo Bus Stop
- Ave. Duration
- 1h 5m
- Frequency
- Every 4 hours
- Estimated price
- $9–15
- Website
- Greyhound
Bus from Detroit Bus Station to Port Authority Bus Terminal
- Ave. Duration
- 17h 15m
- Frequency
- Once daily
- Estimated price
- $110–180
- Website
- Greyhound
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Booking & Getting There
Windsor to Milford bus services, operated by Greyhound USA, arrive at Port Authority Bus Terminal station.
Windsor to Milford train services, operated by VIA Rail, arrive at Aldershot station.
Yes, the driving distance between Windsor to Milford is 644 miles. It takes approximately 12h 8m to drive from Windsor to Milford.
There are 260+ hotels available in Milford.



