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Winchester, VA, USA to Boston, MA, USA from $74: 9 ways by bus, train, flight or car

Compare Travel Options and Prices

from
Winchester, United States of America
to
Boston, United States of America

How to Get from Winchester to Boston: Cheapest, Fastest and Best Way

1Map provides directions to cities, towns, landmarks, attractions, and addresses worldwide, offering thousands of multi-modal routes to easily get you from point A to point B.

$74 by busBest price
698 kmDistance
4h 18m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Winchester to Boston with 1Map travel planner. Easily compare ticket prices, explore various transport options, and find the best routes for a seamless and cost-effective travel experience.

Company
various
Bus
Plane
Average Duration
4h  18m
Estimated price
$180-534
Recommended
Company
various
Bus
Average Duration
12h  33m
Estimated price
$74-221
Cheapest
route map
Distance: 698 km
Duration: 4h 18m

See more options

Company
various
Train
Plane
Average Duration
5h  54m
Estimated price
$125-746
Company
various
Taxi
Bus
Subway
Plane
Average Duration
5h  26m
Estimated price
$138-483
Company
various
Bus
Plane
Train
Average Duration
6h  3m
Estimated price
$227-804
Company
various
Bus
Plane
Train
Average Duration
7h  5m
Estimated price
$1800-1801
Company
various
Train
Average Duration
9h  59m
Estimated price
$1802-1803
Company
various
Bus
Average Duration
12h  33m
Estimated price
$1804-221
Company
various
Drive
Average Duration
8h  46m
Estimated price
$1805-1806
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Traveling From Winchester to Boston

The journey from Winchester to Boston showcases a delightful contrast between the quaint, suburban charm of Winchester and the vibrant, bustling city life of Boston.

Best Neighbourhoods in Boston

Boston's neighborhoods offer distinct experiences and cultural vibes for all visitors.

North End
• Renowned for its authentic Italian cuisine.
• Charming streets and historical sites abound.
Back Bay
• Home to upscale shopping and dining options.
• Stunning Victorian brownstones line the streets.
South Boston
• Known for its beautiful waterfront parks.
• Offers a vibrant nightlife scene.

Best Times To Visit Boston's Attractions

Visiting Boston's top attractions at the right time can elevate your experience.

Freedom Trail
Early mornings or late afternoons are ideal to experience its historic charm minus the crowds.
Boston Common
Spring and fall offer breathtaking scenery with fewer visitors enjoying the park.
Museum of Fine Arts
Weekdays in the late afternoon provide a quieter setting to appreciate the art.

Boston Weather: What to Expect Year-Round

Boston experiences a humid continental climate with four distinct seasons, meaning you can enjoy warm summers and cold winters. Spring and fall are often the best times to visit, offering mild temperatures that enhance your traveling experience.

Dining Recommendation in Boston

You can’t leave Boston without trying the clam chowder at Union Oyster House, the oldest continuously operating restaurant in the U.S. This dish packs a punch with its rich, creamy texture and fresh local seafood, providing a lively dining atmosphere that sharply contrasts with the more subdued culinary style often found in Winchester.

Winchester - Boston operators

Explore transport companies operating between Winchester and Boston, with prices starting at . These companies offer competitive pricing, flexible schedules, and comfortable travel experiences.

Bus
Contact phone
+1-800-827-3490
Website
virginiabreeze.org

Bus from Front Royal to Dulles International Airport

Average Duration
1h 5m
Estimated price
$22129-7473

Bus from Crooked Run Park and Ride to Washington Union Station

Average Duration
2h 10m
Estimated price
$7472-7477
Contact phone
+1 (855) 626-8585
Website
flixbus.com

Bus from Washington Union Station to New York Midtown

Average Duration
4h 25m
Estimated price
$7470-746

Bus from New York Midtown to Boston

Average Duration
4h 20m
Estimated price
$22129-22130
Contact phone
+1 214-849-8100
Website
greyhound.com

Bus from Washington Union Station to Port Authority Bus Terminal

Average Duration
4h 25m
Estimated price
$7475-22130

Bus from Port Authority Bus Terminal to Boston

Average Duration
4h 30m
Estimated price
$7473-5345
Contact phone
1-800-343-9999
Website
peterpanbus.com

Bus from Union Station, Washington, DC to Port Authority Bus Terminal

Average Duration
4h 20m
Estimated price
$2215-746

Bus from Port Authority Bus Terminal to South Station, Boston, MA

Average Duration
4h 20m
Estimated price
$2215-22130
Train
Contact phone
+1 202-637-7000
Website
wmata.com

Train from Washington Dulles International Airport, Silver Line Center Platform to Rosslyn, Blue/Orange/Silver Line Track 1 Platform

Average Duration
45m
Estimated price
$747-748
Contact phone
1-866-743-3682
Website
mta.maryland.gov

Train from DUFFIELDS W VA MARC eb to Washington Union Station

Average Duration
1h 51m
Estimated price
$747-2211

Train from Washington Union Station to BWI Thurgood Marshall

Average Duration
35m
Estimated price
$747-2214
Contact phone
+1 800-872-7245
Website
amtrak.com

Train from Washington Union Station to BWI Thurgood Marshall

Average Duration
26m
Estimated price
$22124-1800

Train from Washington Union Station to Boston

Average Duration
9h 58m
Estimated price
$22150-74740
Contact phone
+1 800-872-7245
Website
amtrak.com

Train from Washington Union Station to Boston

Average Duration
6h 51m
Estimated price
$22140-221300
Plane
Website
jetblue.com

Plane from Reagan Washington to Boston

Average Duration
1h 34m
Estimated price
$5343-5344
Website
southwest.com

Plane from Reagan Washington to Boston

Average Duration
1h 35m
Estimated price
$5343-5348
Website
aa.com

Plane from Reagan Washington to Boston

Average Duration
1h 37m
Estimated price
$5343-5348
Website
united.com

Plane from Washington Dulles to Boston

Average Duration
1h 35m
Estimated price
$1806-53450
Taxi
Contact phone
+1 540-662-4111

Taxi from Winchester to Front Royal

Average Duration
23m
Estimated price
$7490-22150
Drive

Drive from Winchester to Boston

Average Duration
8h 46m
Estimated price
$1805-1806

Frequently asked questions

Find out more about the route from Winchester to Boston.

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The distance between Winchester and Boston is approximately 500 miles. If you're driving, the journey typically takes around 8 to 9 hours, depending on traffic and route. By train, it usually takes about 10 to 12 hours with transfers, while flying is the quickest option, taking around 1.5 to 2 hours of flight time, not including airport security and travel to and from the airport.
The most cost-effective transportation option from Winchester to Boston is typically by bus, which can be both economical and convenient, often taking around 10 to 12 hours. Alternatively, if you book in advance, flying may offer competitive prices and can save significant travel time, with flights taking about 1.5 to 2 hours, plus additional time for airport procedures. Train travel can be another efficient option, but it might not be as cost-effective unless you find special fare deals. Ultimately, the best choice depends on your budget and how much time you have available for the trip.
Prices for traveling from Winchester to Boston can vary widely depending on the mode of transportation and how far in advance you book. Bus tickets typically range from $30 to $80 one way, while train fares may be higher, usually between $60 and $150, depending on the service and time of booking. Flights can also vary significantly, with prices ranging from $100 to $300 or more, especially during peak travel seasons. It's advisable to compare prices across different transportation options to find the best deal for your travel dates.
To travel from Winchester to Boston without using public transportation, you can consider driving your own vehicle or renting a car for the trip. Another option is to arrange a ride with friends or family who may be heading in the same direction. If you prefer a more unique experience, you could look into rideshare services, where you can share a ride with someone who is already making the journey. Additionally, if you enjoy the outdoors, consider exploring the route via bike, though it would require significant planning and preparation for such a long distance.
Traveling from Winchester to Boston without a car can be accomplished by utilizing a combination of rideshare services, such as Uber or Lyft, for shorter segments of the journey. You can also consider booking a private shuttle or van service that offers long-distance rides between cities. Alternatively, you could arrange a ride with friends or family members who might be traveling to Boston. Lastly, if you're flexible with your travel time, consider using a bicycle for part of the trip to enjoy scenic routes along the way.
There is no direct train service from Winchester to Boston so travelers typically need to transfer in locations like Washington, D.C. or via other connecting cities. For bus travel, companies like Greyhound may offer routes that connect these two locations, but they often require transfers as well. Flying is another option, though it usually wouldn't have a direct flight from Winchester itself, and you'd need to travel to a nearby airport, like Dulles International Airport. Overall, while there isn't a direct link, multiple transportation options are available with some connections along the way.
The flight duration between Winchester and Boston is approximately 1.5 to 2 hours, but this can vary based on the specific route and flight conditions. However, since there are no airports directly in Winchester, travelers will first need to drive to a larger airport, such as Dulles International Airport, which can extend the overall travel time. Typical flight prices between Washington, D.C., and Boston can range from $100 to $300, depending on the time of booking and the airline. Additionally, travelers should account for the cost of ground transportation to and from the airport, which can vary significantly.
There are numerous accommodation options near Boston ranging from luxury hotels to budget-friendly motels. Popular neighborhoods for visitors include Back Bay, known for its upscale hotels and shopping, and the historic North End, which offers charming bed-and-breakfasts. For those seeking a quieter stay, Cambridge, just across the river, provides a variety of boutique hotels and is home to Harvard University. Additionally, many travelers consider Airbnb rentals for a more personalized experience in the city.