There are 5 ways to get from Fairfield to Southold by car ferry, car, train, bus, 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.
Car ferry, drive
best- Take the car ferry from Bridgeport to Port Jeffersoncarferry Bridgeport- Port Jefferson
- Drive from Port Jefferson to Southoldcar
2h 20m$29–91Train
- Take the train from Fairfield to Grand Central Terminaltrain
- Take the train from Jamaica to Ronkonkomatrain
- Take the train from Ronkonkoma to Southoldtrain
5h 30m$36–75Car ferry, bus
- Take the car ferry from Bridgeport to Port Jeffersoncarferry Bridgeport- Port Jefferson
- Take the bus from Port Jefferson LIRR to Riverhead LIRRbus 62
5h 33m$37–98Train, car ferry
- Take the train from Bridgeport Amtrak Station to New Londontrain Northeast Regional
- Take the car ferry from New London to Orient Pointcarferry New London
5h 41m$50–147Bus
- Take the bus from Bridgeport Bus Stop to Port Authority Bus Terminalbus Greyhound US0255s
- Take the bus from 41st St bet 3rd & Lex to Southoldbus North Fork
7h 21m$43–102
Fairfield to Southold by train
Questions & Answers
The cheapest way to get from Fairfield to Southold is to train which costs $35 - $75 and takes 5h 30m.
The fastest way to get from Fairfield to Southold is to car ferry and drive which takes 2h 20m and costs $29 - $95.
No, there is no direct bus from Fairfield to Southold. However, there are services departing from Post Rd. at Ruane St. and arriving at Southold via Bridgeport Bus Stop, West 42nd Street & 8th Avenue and 41st St bet 3rd & Lex. The journey, including transfers, takes approximately 7h 21m.
No, there is no direct train from Fairfield to Southold. However, there are services departing from Fairfield and arriving at Southold via Grand Central Terminal, Jamaica and Ronkonkoma. The journey, including transfers, takes approximately 5h 30m.
The distance between Fairfield and Southold is 61 miles.
The best way to get from Fairfield to Southold without a car is to train which takes 5h 30m and costs $35 - $75.
It takes approximately 2h 20m to get from Fairfield to Southold, including transfers.
Fairfield to Southold bus services, operated by Greyhound USA, depart from Bridgeport Bus Stop station.
Fairfield to Southold train services, operated by Metro-North Railroad (MNR), depart from Fairfield station.
The best way to get from Fairfield to Southold is to train which takes 5h 30m and costs $35 - $75. Alternatively, you can bus, which costs $40 - $110 and takes 7h 21m.
What companies run services between Fairfield, CT, USA and Southold, NY, USA?
You can take a train from Fairfield to Southold via Grand Central Terminal, Jamaica, and Ronkonkoma in around 5h 30m. Alternatively, you can take a bus from Post Rd. at Ruane St. to Southold via Bridgeport Bus Stop, Port Authority Bus Terminal, West 42nd Street & 8th Avenue, E 42 St/Lexington Av, and 41st St bet 3rd & Lex in around 7h 21m.
- Phone
- +1 877.690.5114
- Website
- mta.info
Train from Fairfield to Grand Central Terminal
- Ave. Duration
- 1h 33m
- Frequency
- Every 30 minutes
- Estimated price
- $14–23
- Website
- https://www.mta.info/agency/metro-north-railroad
- Schedules at
- https://www.mta.info/schedules
- Off-Peak
- $14–17
- Peak
- $20–23
- Phone
- +1-718-217-5477
- Website
- mta.info
Train from Jamaica to Ronkonkoma
- Ave. Duration
- 59 min
- Frequency
- Every 30 minutes
- Estimated price
- $8–21
- Website
- https://www.mta.info/agency/long-island-rail-road
- Schedules at
- https://www.mta.info/agency/long-island-rail-road/timetables
- Off-Peak
- $8–12
- Peak
- $16–21
Train from Ronkonkoma to Southold
- Ave. Duration
- 1h 14m
- Frequency
- 3 times a day
- Estimated price
- $8–22
- Website
- https://www.mta.info/agency/long-island-rail-road
- Schedules at
- https://www.mta.info/agency/long-island-rail-road/timetables
- Off-Peak
- $8–12
- Peak
- $17–22
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Bridgeport Amtrak Station to New London
- Ave. Duration
- 1h 9m
- Frequency
- Every 3 hours
- Estimated price
- $21–45
- Website
- https://www.amtrak.com/home.html
- Phone
- 631 852 5200
- [email protected]
- Website
- sctbus.org
Bus from Port Jefferson LIRR to Riverhead LIRR
- Ave. Duration
- 1h 3m
- Frequency
- Hourly
- Estimated price
- $3
- Schedules at
- sctbus.org
- Adults
- $3
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- greyhound.com
Bus from Bridgeport Bus Stop to Port Authority Bus Terminal
- Ave. Duration
- 2h 20m
- Frequency
- Once daily
- Estimated price
- $8–17
- Website
- https://www.greyhound.com/
- Phone
- +1 631.283.4600
- Website
- hamptonjitney.com
Bus from 41st St bet 3rd & Lex to Southold
- Ave. Duration
- 2h 25m
- Frequency
- Once daily
- Estimated price
- $30–75
- Website
- https://www.hamptonjitney.com/hjmobile/
- Schedules at
- https://www.hamptonjitney.com/booking/jitney/schedules.php
- Book at
- https://www.hamptonjitney.com/booking/jitney/tripfinder.php
- Onboard
- $40–50
- Ambassador
- $60–75
- Prepaid Online Rate
- $30–40
- Phone
- +1 888-443-3779
- [email protected]
- Website
- 88844ferry.com
Car ferry from Bridgeport to Port Jefferson
- Ave. Duration
- 1h 15m
- Frequency
- Hourly
- Estimated price
- $22–80
- Website
- https://www.88844ferry.com
- Schedules at
- https://www.88844ferry.com/schedule
- Car and passenger
- $78–80
- Adult
- $25
- Senior
- $22
Car ferry from Bridgeport to Port Jefferson
- Ave. Duration
- 1h 15m
- Frequency
- Hourly
- Estimated price
- $22–80
- Website
- https://www.88844ferry.com
- Schedules at
- https://www.88844ferry.com/schedule
- Car and passenger
- $78–80
- Adult
- $25
- Senior
- $22
- Phone
- +1 860-443-5281
- [email protected]
- Website
- longislandferry.com
Car ferry from New London to Orient Point
- Ave. Duration
- 1h 20m
- Frequency
- Hourly
- Estimated price
- $20–90
- Schedules at
- longislandferry.com
- Passenger
- $20–23
- Vehicle and Passenger
- $70–90
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More Questions & Answers
Fairfield to Southold bus services, operated by Greyhound USA, arrive at Port Authority Bus Terminal station.
Fairfield to Southold train services, operated by Metro-North Railroad (MNR), arrive at Grand Central Terminal station.
There are 238+ hotels available in Southold.


















