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How to get fromChester to Windsorby bus, train, car, bus (Greyhound), or train (Amtrak)

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There are 6 ways to get from Chester to Windsor by bus, train, car, bus (Greyhound), or train (Amtrak)

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

  1. Bus, train via New Haven

    best
    1. Take the bus from Chester Park Ride to Port Authority Bus Terminalbus bus
    2. Take the train from Ny Moynihan Train Hall At Penn Station to New Haventrain train
    3. Take the train from New Haven to Windsortrain train
    5h 52m
    $42–653

  2. Drive 116.9 mi

    cheapest
    1. Drive from Chester to Windsorcar car 116.9 mi
    2h 32m
    $22–31

  3. Bus via New York

    1. Take the bus from Chester Park Ride to Port Authority Bus Terminalbus bus ShortLine Hudson
    2. Take the bus from New York to Hartfordbus bus Ppb 5623 / ...
    6h 2m
    $38–91

  4. Bus, train

    1. Take the bus from Chester Park Ride to Port Authority Bus Terminalbus bus ShortLine Hudson
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Windsortrain train Northeast Regional
    5h 56m
    $47–105

  5. Bus

    1. Take the bus from Chester Park Ride to Port Authority Bus Terminalbus bus ShortLine Hudson
    2. Take the bus from Port Authority Bus Terminal to Hartford Union Stationbus bus Greyhound US0230 / ...
    6h 32m
    $31–66

  6. Train

    1. Take the train from Harriman to Secaucus Lower Leveltrain train
    2. Take the train from Ny Moynihan Train Hall At Penn Station to New Haventrain train
    3. Take the train from New Haven to Windsortrain train
    6h 51m
    $39–665

Chester to Windsor by bus, foot, and train

Calendar53Weekly Services
Duration5h 52mAverage Duration
Ticket$42Cheapest Price
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Questions & Answers

Map of how to get from Chester to Windsor.ExpandLaunch map view
  • Distance: 182.7 mi
  • Duration: 5h 52m

What companies run services between Chester, NY, USA and Windsor, CT, USA?

You can take a bus from Chester Park Ride to Central St @ Broad St via Port Authority Bus Terminal, New York, Hartford Union Station, and Central Row South Side @ Travelers in around 6h 2m. Alternatively, you can take a bus from Rt 17M & Moffat Ln to Windsor via Metro North Station - Harriman, Harriman, Secaucus Upper Level, Penn Station, Ny Moynihan Train Hall At Penn Station, and New Haven in around 6h 51m.

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