- Must visit
Museum Of The Shenandoah Valley
Regional art, history, and gardens museum with changing exhibitions and a notable house museum on a large landscaped estate.
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The cheapest and fastest trains from New York, NY to Winchester, VA
Showing times and prices for May 20
Cheapest price
$226
Average price
$226
Fastest journey
9 h 14 m
Average duration
9 h 14 m
Trains per day
1
Distance
393 km
Cheap tickets
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 $226 if you buy it on the day, but the cheapest tickets can be found for only $226.
Fast trains
Of the 1 trains that leave New York, NY for Winchester, VA on Wed, May 20, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Wed, May 20 the direct trains cover the 393 km distance in an average of 9 h 14 m but if you time it right, some trains will get you there in just 9 h 14 m .
On Wed, May 20 the slowest trains will take 9 h 14 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.
12:23 PM9h14New York, NY9:37 PMWinchester, VA$2261One-way0 transfers
- 12:23 PM9h14New York, NY9:37 PMWinchester, VA$2261One-way0 transfers
Travel Information
Compare flight and train 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 $70. 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 $70, and a train costs an average of $58.
Distance: 244 miles (393 km)
Compare train with
Most popular Train | Flight | Driving |
|---|---|---|
$223 Average price | $194 Average price Cheapest | $68 Average price (fuel + tolls) |
5h 33m Average total duration 5h 3m 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 |
The cheapest way to travel from New York, NY to Winchester, VA is a flight with an average price of $194 (€157).
This is compared to other travel options from New York, NY to Winchester, VA:
A flight is $29 (€23) less than a train for this route with tickets for a train from New York, NY to Winchester, VA costing on average $223 (€180).
The fastest way to travel from New York, NY to Winchester, VA is by flight with an average journey time of 1h 31m.
Other travel options to Winchester, VA take longer:
Train takes on average 5h 3m.
It's helpful to compare your options as there are 2 ways to travel between New York, NY and Winchester, VA including taking a flight and train.
We recommend using the train as it is the most popular way to get from New York, NY to Winchester, VA among Omio's users.
Take the train. It's the cheaper option, and the extra time on board is usually more relaxing than driving it.
Tickets start at around $223 (€180) compared to roughly $68 (€55) in fuel and tolls — a saving of about $-154.81 (€-125.10). The journey takes 5h 3m 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, Tuesday, May 19. You can also manually refresh the results below to see updated train journeys.
Last updated at
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| 4:11 PM New York, NY | 6h26 | 10:37 PM Winchester, VA | 0 transfersDirect | |
| 4:35 PM New York, NY | 6h02 | 10:37 PM Winchester, VA | 0 transfersDirect | |
This is the last train of the day. | |||||
Find all the dates and times for this journey
Compare prices and tickets New York, NY to Winchester, VA by flight or train
Compare flight and train 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.
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May 20
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Journey information
Overview: Train from New York, NY to Winchester, VA
USAUSA
Trains from New York, NY to Winchester, VA run on average 3 times per day, taking around 5h 3m. Cheap train tickets for this journey start at $58 (€47) 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 2m.
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Distance 244 miles (393 km) |
Average train duration 5h 3m |
Cheapest ticket price $58 (€47) |
Trains per day 3 |
Fastest train 6h 2m |
First train 8:10 AM |
Last train 11:35 AM |
Cheapest Month Nov |
Cheapest Day Tue |
High Season Jan - Mar |
Low Season Oct - Dec |
Best time to book 35 days |
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Train companies: Amtrak from New York, NY to Winchester, VA trainsAmtrak trains will get you between New York, NY and Winchester, VA from $58 (€47). With over 1000 travel companies on Omio, you can find the best train times and tickets for your trip.
Amtrak
About
Amtrak is the main passenger train operator in the United States, providing medium- and long-distance intercity services across 46 states and three Canadian provinces. Operating over 300 trains daily and serving more than 500 destinations, Amtrak connects cities and regions nationwide through routes such as the high-speed Acela in the Northeast Corridor, the scenic Coast Starlight along the West Coast, and the Empire Builder linking Chicago to the Midwest and the Pacific Northwest. Other notable services include the Northeast Regional, Keystone Service, and the unique Auto Train, which allows passengers to bring their cars onboard. Amtrak offers a variety of classes to suit different budgets and travel needs, including Coach, Business, First Class, and Sleeper Class with options like Roomettes, Bedrooms, and Bedroom Suites for overnight journeys. Ticket types include Saver, Value, Flexible, Business, and Premium. Onboard amenities vary by service but may include comfortable seating, Wi-Fi, power outlets, dining options, and lounge access on select trains. Popular routes include Washington, D.C.–Boston, San Diego–San Luis Obispo, San Jose–Sacramento, and Chicago–Seattle.
Luggage & cancellation policy
Average Duration
6h 2m
Cheapest Price
$58 (€47)
Amtrak frequency
2 a day
Luggage included
2 personal items and 2 carry-on bags included free
Luggage storage
Overhead racks, under seats, and designated luggage areas at end of cars
Cancellation Policy
Cancellation policies depend on ticket type and timing
Refund
Full refund if train is canceled by Amtrak
Amenities on board the train
Wifi
Food sold onboard
Café car with snacks, beverages, and light meals. Long-distance trains have full-service dining cars
Seat reservation
Included in ticket price for Business and First Class. Optional fee for Coach Class
Toilets
USB plugs
Accessibility
Wheelchair spaces, accessible restrooms, Red Cap assistance service, accessible platforms and stations
Pets
Small pets under 20 pounds allowed for $26 fee. Must be in carrier. Service animals travel free
Quiet zone
Complete guide to Winchester
Things to do in Winchester
Discover the best of Winchester — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Winchester trip today.
- Recommended
Stonewall Jackson's Headquarters Museum
Historic house museum interpreting Confederate General Thomas J. Jackson's Winchester headquarters and Civil War history.
- Recommended
Shenandoah Valley Civil War Museum
Museum inside the historic Old Court House featuring Civil War artifacts and local Valley history exhibits.
- Must visit
Old Town Winchester
Historic pedestrian-friendly downtown district with preserved architecture, shops, events, and the city's main visitor atmosphere.
- Must visit
Loudoun Street Mall
Walkable downtown main street lined with historic buildings, public art, and seasonal events; a social-media favorite in the city center.
- Recommended
Museum Of The Shenandoah Valley Gardens
Formal and woodland gardens on the museum grounds, popular for scenic walks, photography, and seasonal color.
- Gluten-free
Virginia Ham
Salt-cured, aged country ham long associated with Virginia. It is prized for its intense savory flavor and is often served in biscuits or with red-eye gravy.
Ham Biscuits
A classic Shenandoah Valley and Virginia snack: thin slices of salty country ham tucked into soft biscuits, commonly served at gatherings and local cafes.
Chicken And Dumplings
A comforting regional favorite found across the Shenandoah Valley, featuring stewed chicken and soft dumplings in a rich broth.
Violino Ristorante Italiano
Well-regarded Italian restaurant known for classic pasta dishes, attentive service, and a more refined dining setting.
Bonnie Blue Southern Market & Bakery
Popular local spot for Southern comfort food, biscuits, bakery items, and a relaxed neighborhood feel.
Union Jack Pub & Restaurant
Established Old Town pub serving British and American comfort food with a lively, casual atmosphere and broad menu.
United States Dollar
Prices are moderate by U.S. standards. Casual dining is affordable, while hotels and fine dining cost more.
Average meal costs
- Budget
- USD 10-15 for fast food or a simple lunch.
- Mid-range
- USD 18-35 per person at a casual restaurant.
- Fine dining
- USD 50+ per person at upscale restaurants.
- Coffee
- USD 3-6 for drip coffee or a latte.
Tipping culture
Tip 18-20% in restaurants. Tip USD 1-2 per drink at bars, round up taxis, and tip hotel staff USD 2-5 for help.
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.
Train ticket prices from New York, NY to Winchester, VA can vary. The cheapest ticket starts at $58 (€47), while the average price is around $223 (€180).
The train from New York, NY to Winchester, VA takes 6h 2m and runs 3 per day.
The distance by train from New York, NY to Winchester, VA is 244 miles (393 km).
The first train from New York, NY to Winchester, VA leaves at 8:10 AM.
The last train from New York, NY to Winchester, VA leaves at 11:35 AM.
There is no high speed train available from New York, NY to Winchester, VA.
There is no direct train service currently available from New York, NY to Winchester, VA.
Unfortunately, there is no night train available from New York, NY to Winchester, VA.
The train station in New York, NY that goes to Winchester, VA is Penn Station, New York, NY, which connects to Martinsburg Station, Martinsburg, WV.
The cheapest way to get from New York, NY to Winchester, VA is by train, with a cost of around $58 (€47).
The train journey from New York, NY to Winchester, VA offers scenic views, particularly as it passes through the rolling hills and lush landscapes of the Shenandoah Valley, offering a picturesque experience for travelers.
A day trip from New York, NY to Winchester, VA is not feasible as the travel duration is 6h 2m and the trip occurs 2 times per day for trains, covering a distance of 244 miles (393 km).
To fully explore Winchester, VA, including its historic sites, local wineries, and the scenic Shenandoah Valley, plan to spend around 2 to 3 days.
Yes, you can take the train from New York, NY to Winchester, VA.
Since neither New York, NY nor Winchester, VA are in the Schengen Area, passport requirements depend on the specific immigration rules of United States and United States. Entry and visa requirements can be subject to change. For the latest information, check with your destination's embassy or consulate.
We recommend using the train as it is the most popular way to get from New York, NY to Winchester, VA among Omio's users.
Items not allowed on trains typically include hazardous materials such as explosives, flammable liquids, corrosive substances, and illegal drugs. Additionally, large or bulky items that may obstruct aisles or emergency exits, as well as pets without proper carriers, may be restricted. Specific prohibited items can vary by train operator and region, so please check the rules for your particular journey.
The currency used in the United States is the US Dollar (USD). For travelers, using cards is generally more convenient and widely accepted, especially credit and debit cards, while cash is useful for small purchases or places that do not accept cards.
In Winchester, VA, travelers should be cautious of pickpocketing and petty theft, especially in crowded areas and during events like the Shenandoah Apple Blossom Festival. Common scams include overcharging by unlicensed taxi or ride-share drivers and fraudulent ticket sales for local attractions. Staying aware of surroundings and using official transportation services helps ensure a safe visit.
Pack lightweight, versatile clothing suitable for the destination's climate, and use secure, lockable luggage to protect belongings. Keep essential items like travel documents, medication, and valuables in a carry-on bag for easy access. Use packing organizers or cubes to maximize space and maintain order. Lastly, include a small first aid kit and personal hygiene items for added comfort during travel.
popular train stations
Popular train stations from New York, NY to Winchester, VA
New York
Winchester
Amenities at train station
Wifi
Lockers
Parking
Dining
ATM
Taxis
Accessibility
Hotel
Ticket Office
Car Rental
Information Deskinformation
Ticket Office Hours
- Mon - Sun: 05:00-22:00
Distance to city center
4 kmWifi
- Free Wi-Fi available in Moynihan Train Hall.
Lockers
- Baggage assistance is provided by Red Caps, open 24/7 at Penn and open from 05:00 to 23:00 at Moynihan Train Hall.
Dining
- 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
Accessibility
- Accessible facilities including restroom, parking, elevators, and ramps. Additional assistance available at ticket counters or by asking uniformed employees.
Hotel
- The New Yorker at Wyndham Hotel
- Courtyard by Marriott New York Manhattan/Chelsea
- Hilton Garden Inn West 35th Street
Ticket Office
- Mon - Sun: 05:00-22:00
Information Desk
- Located on the connecting concourse near Tracks 18-19.
Public transit options for Penn Station
- 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
Here are some other resources that might have the information you need
Most popular trains to and from Winchester, VA and New York, NY
Most popular train connections to Winchester, VA
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