The cheapest and fastest trains from New York, NY to Winchester, VA
Cheapest price
$121
Average price
$192
Fastest journey
6 h 35 m
Average duration
7 h 25 m
Trains per day
4
Distance
393 km
The best way to find a cheap train ticket from New York, NY to Winchester, VA is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from New York, NY to Winchester, VA will cost around $192 if you buy it on the day, but the cheapest tickets can be found for only $121.
It's difficult to get from New York, NY to Winchester, VA without transferring at least once.
119 Northeast Regional · 40 Floridian
95 Northeast Regional · 40 Floridian
141 Northeast Regional · 40 Floridian
2155 Acela+
40 Floridian
119 Northeast Regional · 40 Floridian
2155 Acela+
40 Floridian
95 Northeast Regional · 40 Floridian
141 Northeast Regional · 40 FloridianTravel Information
Compare train and flight for New York, NY to Winchester, VA
Omio recommends booking the train as it is the most popular option from New York, NY to Winchester, VA among Omio's users. If you are prioritising price take the train with prices starting from €59. For those with little time consider booking a flight which can get you there in 1h 34m. The ticket price range depends on the travel mode: a train costs an average of €59, and a flight costs an average of €63.
Distance: 244 miles (393 km)
Compare train with
Most popular Train | Flight |
|---|---|
€156 Average price Cheapest | €176 Average price |
5h 28m Average total duration 4h 58m Onboard + 30m Additional time* | 4h 34m Average total duration Fastest 1h 34m Onboard + 3h 0m Additional time* |
![]() Most popular train company | ![]() Most popular airline |
Direct Options | Direct Options |
Live departures
New York, NY to Winchester, VA train times
The table below shows live departures for New York, NY to Winchester, VA trains for today, Tuesday, November 18. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
141 Northeast Regional · 40 Floridian | 1:10 PM Penn Station, New York, NY | 9h27 | 10:37 PM Martinsburg Station, Martinsburg, WV | 1 transfer | |
95 Northeast Regional · 40 Floridian | 3:35 PM Penn Station, New York, NY | 7h02 | 10:37 PM Martinsburg Station, Martinsburg, WV | 1 transfer | |
2155 Acela+ 40 Floridian | 4:00 PM Penn Station, New York, NY | 6h37 | 10:37 PM Martinsburg Station, Martinsburg, WV | 1 transfer | |
119 Northeast Regional · 40 Floridian | 4:02 PM Penn Station, New York, NY | 6h35 | 10:37 PM Martinsburg Station, Martinsburg, WV | 1 transfer | |
| Wednesday, November 19 | |||||
![]() | 12:10 PM New York, NY | 9h35 | 9:45 PM Winchester, VA | 0 transfersDirect | |
Find all the dates and times for this journey
Compare prices and tickets New York, NY to Winchester, VA by train or flight
Compare train and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
Nov 19
Nov 20
Nov 21
Nov 22
Nov 23
Nov 24
Nov 25
Journey information
Overview: Train from New York, NY to Winchester, VA
Trains from New York, NY to Winchester, VA run on average 2 times per day, taking around 4h 58m. Cheap train tickets for this journey start at $73 (€59) if you book in advance.
The earliest train runs at 08:10, the last at 11:35. The fastest train covers the 244 miles (393 km) distance in 6h 32m.
Distance 244 miles (393 km) |
Average train duration 4h 58m |
Cheapest ticket price $73 (€59) |
Trains per day 2 |
Fastest train 6h 32m |
First train 08:10 |
Last train 11:35 |
Train companies: Amtrak from New York, NY to Winchester, VA trainsAmtrak trains will get you between New York, NY and Winchester, VA from $73 (€59). With over 1000 travel companies on Omio, you can find the best train times and tickets for your trip.
Amtrak
FAQs: Trains from New York, NY to Winchester, VA
Find answers to the most common questions about traveling from New York, NY to Winchester, VA by train. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest train, the cheapest option, or tips for making the most of your visit at Winchester, VA, this guide helps you travel smarter and with confidence.

popular train stations
Popular train stations from New York, NY to Winchester, VA
- Mon - Sun: 05:00-22:00
- Free Wi-Fi available in Moynihan Train Hall.
- Baggage assistance is provided by Red Caps, open 24/7 at Penn and open from 05:00 to 23:00 at Moynihan Train Hall.
- Blue Bottle Coffee
- Magnolia Bakery
- Starbucks
- The Pennsy Food Hall
- Nick + Stef's Steakhouse
- Penn & Sushi
- Krispy Kreme Donuts
- T.G.I. Friday's
- NY Pizza Suprema
- Blarney Stone
- & many more
- Accessible facilities including restroom, parking, elevators, and ramps. Additional assistance available at ticket counters or by asking uniformed employees.
- The New Yorker at Wyndham Hotel
- Courtyard by Marriott New York Manhattan/Chelsea
- Hilton Garden Inn West 35th Street
- Mon - Sun: 05:00-22:00
- Located on the connecting concourse near Tracks 18-19.
- Subway lines: 1, 2, 3, A, C, E
- Bus lines: M7, M20
- Train lines: Acela, Adirondack, Cardinal, Carolinian, Crescent, Empire Service, Ethan Allen Express, Keystone Service, Lake Shore Limited, Maple Leaf, Northeast Regional, Pennsylvanian, Silver Service/Palmetto, Vermonter, PATH, New Jersey Transit, Long Island Railroad, AirTrain Newark, AirTrain JFK
Most popular train connections from New York, NY
More options for your journey from New York, NY to Winchester, VA
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