The cheapest and fastest trains from New York, NY to Winchester, VA
Cheapest price
zł347
Average price
zł483
Fastest journey
6 h 2 m
Average duration
6 h 14 m
Trains per day
2
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 zł483 if you buy it on the day, but the cheapest tickets can be found for only zł347.
Of the 2 trains that leave New York, NY for Winchester, VA on Tue, Aug 25, 2 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Tue, Aug 25 the direct trains cover the 393 km distance in an average of 6 h 14 m but if you time it right, some trains will get you there in just 6 h 2 m .
On Tue, Aug 25 the slowest trains will take 6 h 26 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.
4:35 PM6h02New York, NY10:37 PMWinchester, VAzł3471One-way0 transfers
4:11 PM6h26New York, NY10:37 PMWinchester, VAzł6181One-way0 transfers
4:35 PM6h02New York, NY10:37 PMWinchester, VAzł3471One-way0 transfers
4:11 PM6h26New York, NY10:37 PMWinchester, VAzł6181One-way0 transfers
Travel 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 flight with prices starting from zł319. For those with little time consider booking a flight which can get you there in 1h 31m. The ticket price range depends on the travel mode: a flight costs an average of zł319, and a train costs an average of zł271.
Distance: 244 miles (393 km)
Compare train with
Most popular Train | Flight | Driving |
|---|---|---|
zł659 Average price | zł512 Average price Cheapest | zł256 Average price (fuel + tolls) |
5h 37m Average total duration 5h 7m Onboard + 30m Additional time* | 4h 31m Average total duration Fastest 1h 31m Onboard + 3h 0m Additional time* | 4h 19m Average total duration (door-to-door) |
![]() Most popular train company | ![]() Most popular airline | Your own car or car rental |
Direct Options | Direct Options | Direct Options |
This is compared to other travel options from New York, NY to Winchester, VA:
A flight is zł147 less than a train for this route with tickets for a train from New York, NY to Winchester, VA costing on average zł659.
Other travel options to Winchester, VA take longer:
Train takes on average 5h 7m.
Tickets start at around zł659 compared to roughly zł256 in fuel and tolls — a saving of about zł-403.12. The journey takes 5h 7m versus 4h 19m by car, so you'll arrive a bit later, but you can work, read, or sleep along the way rather than spending the time behind the wheel. You'll also save the hassle of parking at the other end.
Driving is worth it if you're on a tight schedule, travelling as a group, or want to stop somewhere en route.
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, Monday, August 24. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
141 Northeast Regional · 40 Floridian | 8:23 AM Penn Station, New York, NY | 9h14 | 5:37 PM Martinsburg Station, Martinsburg, WV | 1 transfer | |
141 Northeast Regional · 40 Floridian | 8:39 AM Newark Penn Station, Newark, NJ | 8h58 | 5:37 PM Martinsburg Station, Martinsburg, WV | 1 transfer | |
141 Northeast Regional · 40 Floridian | 8:44 AM Newark Liberty International Airport, Newark, NJ | 8h53 | 5:37 PM Martinsburg Station, Martinsburg, WV | 1 transfer | |
95 Northeast Regional · 40 Floridian | 10:35 AM Penn Station, New York, NY | 7h02 | 5:37 PM Martinsburg Station, Martinsburg, WV | 1 transfer | |
95 Northeast Regional · 40 Floridian | 10:53 AM Newark Penn Station, Newark, NJ | 6h44 | 5:37 PM Martinsburg Station, Martinsburg, WV | 1 transfer | |
2155 NextGen Acela+ 40 Floridian | 11:06 AM Penn Station, New York, NY | 6h31 | 5:37 PM Martinsburg Station, Martinsburg, WV | 1 transfer | |
119 Northeast Regional · 40 Floridian | 11:16 AM Penn Station, New York, NY | 6h21 | 5:37 PM Martinsburg Station, Martinsburg, WV | 1 transfer | |
2155 NextGen Acela+ 40 Floridian | 11:21 AM Newark Penn Station, Newark, NJ | 6h16 | 5:37 PM Martinsburg Station, Martinsburg, WV | 1 transfer | |
119 Northeast Regional · 40 Floridian | 11:32 AM Newark Penn Station, Newark, NJ | 6h05 | 5:37 PM Martinsburg Station, Martinsburg, WV | 1 transfer | |
119 Northeast Regional · 40 Floridian | 11:37 AM Newark Liberty International Airport, Newark, NJ | 6h00 | 5:37 PM Martinsburg Station, Martinsburg, WV | 1 transfer | |
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.
Aug 25
Aug 26
Aug 27
Aug 28
Aug 29
Aug 30
Aug 31
Journey information
Overview: Train from New York, NY to Winchester, VA
Trains from New York, NY to Winchester, VA run on average 3 times per day, taking around 5h 7m. Cheap train tickets for this journey start at zł271 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 5h 7m |
Cheapest ticket price zł271 |
Trains per day 3 |
Fastest train 6h 32m |
First train 8:10 AM |
Last train 11:35 AM |
Cheapest Month Jun |
Cheapest Day Tue |
High Season Jan - Mar |
Low Season Apr - Jun |
Best time to book 35 days |
Train companies: Amtrak from New York, NY to Winchester, VA trainsAmtrak trains will get you between New York, NY and Winchester, VA from zł271. 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
Most New York, NY to Winchester, VA trains use the Penn Station to Martinsburg Station station pair. Use this guide to compare New York, NY and Winchester, VA train stations on this route, check city-centre transport, alongside checking practicalities like train station facilities and services.
Which New York, NY station do trains to Winchester, VA leave from?
Getting to Penn Station from New York city centre
Penn Station is 4 km from New York city centre. Public transport options include:
Penn Station train station facilities and services
Penn Station has practical services for this route, including Wifi, Lockers, Parking, Dining, ATM, Taxis, Accessibility, Hotel, Ticket Office, Car Rental, and Information Desk.
Food and drink
Food options include: 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
Wi-Fi and ATMs
Free Wi-Fi available in Moynihan Train Hall. ATMs are there are ATMs in various locations around the station.
Tickets and information
The ticket office is open Mon - Sun: 05:00-22:00. Information desks are located on the connecting concourse near Tracks 18-19.
Luggage and lost property
Luggage storage is baggage assistance is provided by Red Caps, open 24/7 at Penn and open from 05:00 to 23:00 at Moynihan Train Hall. .
Parking, taxis and toilets
Available at Penn Station: Parking, Taxis.
Bike and car services
Available at Penn Station: Car Rental.
Accessibility
Accessibility facilities are available at Penn Station: Accessible facilities including restroom, parking, elevators, and ramps. Additional assistance available at ticket counters or by asking uniformed employees.
Shops, hotels and contact
Nearby hotels include The New Yorker at Wyndham Hotel, Courtyard by Marriott New York Manhattan/Chelsea, Hilton Garden Inn West 35th Street.
Most popular train connections from New York, NY
More options for your journey from New York, NY to Winchester, VA
Here are some other resources that might have the information you need


