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How to get fromMiddlebury to Portlandby bus (Amtrak), train (Amtrak), car, train, plane, bus (Greyhound, Flixbus), or bus

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There are 8 ways to get from Middlebury to Portland by bus (Amtrak), train (Amtrak), car, train, plane, bus (Greyhound, Flixbus), or bus

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 W Main St @ Leavenworth St to Asylum St @ Bushnell Parkbus bus 928
    2. Take the bus from Hartford Union Station to South Stationbus bus
    3. Take the bus from Boston, MA - South Station to Portland, MEbus bus
    7h 7m
    $45–108

  2. Bus via City of Portland

    cheapest
    1. Take the bus from W Main St @ Leavenworth St to Asylum St @ Bushnell Parkbus bus 928
    2. Take the bus from Hartford Union Station to Bostonbus bus
    3. Take the bus from Boston to City of Portlandbus bus
    7h 17m
    $34–67

  3. Train

    1. Take the train from Waterbury to Bridgeporttrain train
    2. Take the train from Bridgeport Amtrak Station to Bostontrain train
    3. Take the train from Boston to Portlandtrain train
    9h 27m
    $101–224

  4. Drive 233.4 mi

    1. Drive from Middlebury to Portlandcar car 233.4 mi
    4h 11m
    $43–62

  5. Train, train to Laguardia Airport, fly

    1. Take the train from Waterbury to Bridgeporttrain train
    2. Take the train from Bridgeport to 125th Street - Harlemtrain train
    3. Fly from Laguardia Airport (LGA) to Portland (PWM)plane plane LGA - PWM
    6h 26m
    $96–482

  6. Train, bus

    1. Take the train from New Haven to Bostontrain train Northeast Regional
    2. Take the bus from Boston, MA - South Station to Portland, MEbus bus Logan Airport / ...
    8h
    $60–706

  7. Train, train to John F. Kennedy International Airport, fly

    1. Take the train from Waterbury to Bridgeporttrain train
    2. Take the train from Bridgeport to Grand Central Terminaltrain train
    3. Fly from John F. Kennedy International Airport (JFK) to Portland (PWM)plane plane JFK - PWM
    6h 41m
    $92–393

  8. Train, train to Newark Liberty International Airport, fly

    1. Take the train from Waterbury to Bridgeporttrain train
    2. Take the train from Bridgeport Amtrak Station to Ny Moynihan Train Hall At Penn Stationtrain train
    3. Fly from Newark Liberty International Airport (EWR) to Portland (PWM)plane plane EWR - PWM
    7h 12m
    $551–1,389

Middlebury to Portland by bus

Calendar10Weekly Buses
Duration7h 7mAverage Duration
Ticket$45Cheapest Price
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Questions & Answers

Map of how to get from Middlebury to Portland.ExpandLaunch map view
  • Distance: 244.7 mi
  • Duration: 7h 7m

What companies run services between Middlebury, CT, USA and Portland, ME, USA?

You can take a bus from Village Green @ North St to Portland, ME via West Main St @ Leavenworth St, W Main St @ Leavenworth St, Asylum St @ Bushnell Park, Hartford Union Station, South Station, and Boston, MA - South Station in around 7h 7m. Alternatively, you can take a bus from Village Green @ North St to Portland via W Main St @ State St, Waterbury, Bridgeport, Bridgeport Amtrak Station, Boston, Back Bay, North Station, and Boston in around 9h 27m.

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