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How to Travel from

Winchester to Long Island

by Plane, Train, Route or Car

Winchester
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Long Island
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Winchester
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Long Island
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Schedule

Winchester, United States of America → Long Island, United States of America

All
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April 2026
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October 2026
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Fourteen ways to Travel from Winchester to Long Island

Composite routes from Winchester to Long Island

Cheapest
Other

Transport providers

Airlines

JetBlue Airways

Website:
jetblue.com/
Plane from General Edward Lawrence Logan International Airport to John
Ave. Duration:
1h 23m
Frequency:
Every day
Estimated price:
$60.11–$626.63
Plane from General Edward Lawrence Logan International Airport to Laguardia
Ave. Duration:
1h 19m
Frequency:
Every day
Estimated price:
$95.91–$537.11
Plane from General Edward Lawrence Logan International Airport to Macarthur
Ave. Duration:
1h 8m
Frequency:
Wednesday to Friday
Estimated price:
$70.34–$345.29
Plane from Ronald Reagan Washington National Airport to John
Ave. Duration:
1h 14m
Frequency:
Monday and Sunday
Estimated price:
$108.70–$498.75

American Airlines

Website:
aa.com/
Plane from General Edward Lawrence Logan International Airport to John
Ave. Duration:
1h 26m
Frequency:
Every day
Estimated price:
$83.12–$396.44
Plane from General Edward Lawrence Logan International Airport to Laguardia
Ave. Duration:
1h 21m
Frequency:
Every day
Estimated price:
$345.29–$601.05
Plane from Ronald Reagan Washington National Airport to John
Ave. Duration:
1h 22m
Frequency:
Every day
Estimated price:
$153.46–$422.02
Plane from Ronald Reagan Washington National Airport to Laguardia
Ave. Duration:
1h 18m
Frequency:
Every day
Estimated price:
$166.25–$460.38

Delta

Website:
delta.com/
Plane from General Edward Lawrence Logan International Airport to John
Ave. Duration:
1h 30m
Frequency:
Every day
Estimated price:
$60.11–$255.77
Plane from General Edward Lawrence Logan International Airport to Laguardia
Ave. Duration:
1h 26m
Frequency:
Every day
Estimated price:
$63.94–$268.56
Plane from Washington Dulles International Airport to John
Ave. Duration:
1h 25m
Frequency:
Every day
Estimated price:
$61.38–$242.98
Plane from Ronald Reagan Washington National Airport to John
Ave. Duration:
1h 25m
Frequency:
Every day
Estimated price:
$63.94–$268.56
Plane from Ronald Reagan Washington National Airport to Laguardia
Ave. Duration:
1h 16m
Frequency:
Every day
Estimated price:
$70.34–$294.13

United Airlines

Website:
united.com/
Plane from Washington Dulles International Airport to Laguardia
Ave. Duration:
1h 26m
Frequency:
Every day
Estimated price:
$204.61–$601.05

Southwest Airlines

Website:
southwest.com/
Plane from Baltimore-Washington International Airport to Macarthur
Ave. Duration:
1h 10m
Frequency:
Every day
Estimated price:
$127.88–$447.59

Train operators

Amtrak

Phone:
+1 800-872-7245
Website:
amtrak.com/home.html
Train from Washington Union Station to Ny
Ave. Duration:
3h 20m
Frequency:
4 times a day
Estimated price:
$30.69–$127.88
Train from Washington Union Station to BWI
Ave. Duration:
37 min
Frequency:
Hourly
Estimated price:
$6.39–$70.34

Amtrak Northeast Regional

Phone:
+1 800-872-7245
Website:
amtrak.com/home.html
Train from Boston to Ny
Ave. Duration:
4h 21m
Frequency:
Every 3 hours
Estimated price:
$38.37–$255.77
Train from Boston to New
Ave. Duration:
1h 27m
Frequency:
Every 4 hours
Estimated price:
$24.30–$242.98
Train from Boston to Bridgeport
Ave. Duration:
2h 36m
Frequency:
Every 4 hours
Estimated price:
$31.97–$255.77
Train from Washington Union Station to Ny
Ave. Duration:
3h 30m
Frequency:
Hourly
Estimated price:
$37.09–$255.77
Train from Washington Union Station to BWI
Ave. Duration:
27 min
Frequency:
Hourly
Estimated price:
$16.62–$242.98

Amtrak Acela

Phone:
+1 800-872-7245
Website:
amtrak.com/home.html
Train from Boston to Ny
Ave. Duration:
3h 40m
Frequency:
Every 4 hours
Estimated price:
$60.11–$575.48
Train from Washington Union Station to Ny
Ave. Duration:
2h 48m
Frequency:
Every 2 hours
Estimated price:
$58.83–$562.69
Train from Washington Union Station to BWI
Ave. Duration:
20 min
Frequency:
5 times a day
Estimated price:
$21.74–$383.65

Maryland Transit

Phone:
1-866-743-3682
Website:
mta.maryland.gov
Train from DUFFIELDS W VA MARC eb to Washington
Ave. Duration:
1h 51m
Frequency:
Twice daily
Estimated price:
$2.30–$15.35
Train from Washington Union Station to BWI
Ave. Duration:
35 min
Frequency:
Hourly
Estimated price:
$2.30–$10.23

Long Island Rail Road

Phone:
+1-718-217-5477
Website:
mta.info/agency/long-island-rail-road
Train from New York Penn Station to Ronkonkoma
Ave. Duration:
1h 22m
Frequency:
Every 30 minutes
Estimated price:
$3.71–$25.58
Train from Jamaica to Ronkonkoma
Ave. Duration:
1h
Frequency:
Every 30 minutes
Estimated price:
$3.71–$21.74
Train from Woodside to Ronkonkoma
Ave. Duration:
1h 10m
Frequency:
Hourly
Estimated price:
$3.71–$23.02
Train from Jamaica to Brentwood
Ave. Duration:
47 min
Frequency:
Every 30 minutes
Estimated price:
$3.71–$19.18

Bus operators

Virginia Breeze

Phone:
+1-800-827-3490
Website:
virginiabreeze.drpt.virginia.gov
Bus from Crooked Run Park to Ride
Ave. Duration:
1h 5m
Frequency:
Once daily
Estimated price:
$21.74–$26.86

Hampton Jitney Inc.

Phone:
+1 631.283.4600
Website:
hamptonjitney.com
Bus from B. Heights-Tillary St & Cadman Plz E to Old
Ave. Duration:
2h 56m
Frequency:
On demand
Estimated price:
$33.25–$83.12

Wanda Coach

Phone:
+1 646-630-7186
Website:
wandacoach.com
Bus from Winchester to New
Ave. Duration:
6h
Frequency:
3 times a week
Estimated price:
$38.37–$115.10

Omniride

Phone:
+1 703-730-6664
Website:
omniride.com
Bus from Crooked Run Park & Ride to Virginia
Ave. Duration:
1h 18m
Frequency:
Twice daily
Estimated price:
$8.31–$25.58

Suffolk County Transit

Phone:
+1 (631) 665-3245
Website:
suffolkbus.com/transit/
Bus from Orient Point Ferry Dock to Riverhead
Ave. Duration:
1h 5m
Frequency:
Hourly
Estimated price:
$2.61
Bus from Patchogue LIRR to NYS
Ave. Duration:
16 min
Frequency:
Hourly
Estimated price:
$2.61

Other operators

The Bridgeport and Port Jefferson Steamboat Company

Phone:
+1 888-443-3779
Website:
88844ferry.com
Other from Bridgeport to Port
Ave. Duration:
1h 15m
Frequency:
Hourly
Estimated price:
$23.12–$92.08

Long Island Ferry

Phone:
+1 860-443-5281
Website:
longislandferry.com
Other from New London to Orient
Ave. Duration:
1h 20m
Frequency:
Hourly
Estimated price:
$23.02–$95.91

Questions and Answers

What is the cheapest way to get from Winchester to Long Island?

The cheapest way to get from Winchester to Long Island is to drive which costs $43.48 - $65.22 and takes 4h 38m.

What is the fastest way to get from Winchester to Long Island?

The fastest way to get from Winchester to Long Island is to drive which takes 4h 38m and costs $43.48 - $65.22 .

How far is it from Winchester to Long Island?

The distance between Winchester and Long Island is 474 km. The road distance is 394.5 km.

How do I travel from Winchester to Long Island without a car?

The best way to get from Winchester to Long Island without a car is to train which takes 7h 13m and costs $43.48 - $532.61 .

How long does it take to get from Winchester to Long Island?

It takes approximately 7h 13m to get from Winchester to Long Island, including transfers.

Can I drive from Winchester to Long Island?

Yes, the driving distance between Winchester to Long Island is 395 km. It takes approximately 4h 38m to drive from Winchester to Long Island.

Where can I stay near Long Island?

There are 97+ hotels available in Long Island. Prices start at $74.33 per night.
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