Rome2Rio

How to get fromWindsor to Winchesterby plane, train, bus (Greyhound), bus, car, or taxi

Find Transport to Winchester

See all options

There are 7 ways to get from Windsor to Winchester by plane, train, bus (Greyhound), bus, car, or taxi

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Fly to Bradley International Airport, train

    best
    1. Fly from Detroit (DTW) to Bradley International Airport (BDL)plane plane DTW - BDL
    2. Take the train from Windsor Locks to Brattleboro Stationtrain train
    8h 1m
    $142–545

  2. Drive 614.1 mi

    cheapest
    1. Drive from Windsor to Winchestercar car 614.1 mi
    11h 43m
    $141–203

  3. Bus (Greyhound)

    1. Take the bus from Detroit Bus Station to Cleveland Bus Stationbus bus
    2. Take the bus from Cleveland Bus Station to Springfield Union Stationbus bus
    3. Take the bus from Springfield Union Station to Brattleborobus bus
    18h 50m
    $157–283

  4. Bus, train

    1. Take the bus from Detroit Bus Station to Toledo Bus Stopbus bus
    2. Take the train from Toledo to Springfieldtrain train
    3. Take the train from Springfield to Brattleboro Stationtrain train
    19h 27m
    $280–587

  5. Fly to Boston Logan Airport, train, bus

    1. Fly from Detroit (DTW) to Boston Logan Airport (BOS)plane plane DTW - BOS
    2. Take the train from North Station to Fitchburgtrain train
    3. Take the bus from Fitchburg MA to Athol MAbus bus
    9h 5m
    $497–1,593

  6. Fly to Albany County Airport, bus, line 13 bus, line 10 bus, taxi

    1. Fly from Detroit (DTW) to Albany County Airport (ALB)plane plane DTW - ALB
    2. Take the bus from Albany International Airport to Green Mountain Community Bus Terminalbus bus
    3. Take the bus from GMCN Terminal to Shawsbus bus
    4. Take the bus from Shaws to Brattleboro Transportation Centerbus bus
    5. Take the taxi from Brattleboro Transportation Center to Winchestertaxi taxi
    10h
    $155–714

  7. Train, bus

    1. Take the train from Windsor to Aldershottrain train
    2. Take the train from Aldershot to Albanytrain train
    3. Take the bus from AMTRAK Station Rensselaer to Green Mountain Community Bus Terminalbus bus 7
    19h 30m
    $197–522

Detroit (DTW) to Bradley International Airport (BDL) flights

Calendar52Weekly Planes
Duration3h 10mAverage Duration
Ticket$81Cheapest Price
See schedules

Questions & Answers

Map of how to get from Windsor to Winchester.ExpandLaunch map view
  • Distance: 661.8 mi
  • Duration: 8h 1m

What companies run services between Windsor, ON, Canada and Winchester, NH, USA?

You can take a bus from Detroit Bus Station to Winchester via Cleveland Bus Station, Springfield Union Station, and Brattleboro in around 18h 50m.

Airlines
Train operators
Bus operators
Other operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound