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How to get fromChatham to Winchesterby bus, train, or car

Find Transport to Winchester

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There are 5 ways to get from Chatham to Winchester by bus, train, or car

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

    best
    1. Take the bus from Veterans Field Rd to Hyannis Transportation Centerbus bus H2O Hyannis-Orleans
    2. Take the bus from Hyannis to Bostonbus bus Bz 0947 / ...
    4h 38m
    $22–48
  2. Bus, train

    cheapest
    1. Take the bus from Veterans Field Rd to Cape Cod Hospitalbus bus H2O Hyannis-Orleans
    2. Take the train from Hyannis to South Stationtrain train CapeFLYER
    5h 46m
    $12–35
  3. Drive 95.4 mi

    1. Drive from Chatham to Winchestercar car 95.4 mi
    1h 57m
    $18–26
  4. Bus via Wellington

    1. Take the bus from Veterans Field Rd to Hyannis Transportation Centerbus bus H2O Hyannis-Orleans
    2. Take the bus from Hyannis Transportation Center to Boston South Busesbus bus Hyannis - South Shore to Logan Airport
    4h 49m
    $34–46
  5. Bus via Wellington #2

    1. Take the bus from Veterans Field Rd to Hyannis Transportation Centerbus bus H2O Hyannis-Orleans
    2. Take the bus from Hyannis Transportation Center to Boston South Stationbus bus Hyannis
    4h 51m
    $22–46

Chatham to Winchester by bus, foot, subway, and train

Calendar63Weekly Services
Duration4h 38mAverage Duration
Ticket$22Cheapest Price
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Questions & Answers

What companies run services between Chatham, MA, USA and Winchester, MA, USA?

You can take a bus from Veterans Field Rd to Winchester Center via Hyannis Transportation Center, Hyannis, Boston, Downtown Crossing, North Station, and North Station in around 4h 38m.

Train operators
Bus operators

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