Rome2Rio

How to get fromAnnapolis to Westportby bus, plane, train, bus (Flixbus, Greyhound), car, or train (Amtrak)

Find Transport to Westport

See all options

There are 7 ways to get from Annapolis to Westport by bus, plane, train, bus (Flixbus, Greyhound), car, 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, fly to Westchester County Airport

    best
    1. Take the bus from Annapolis to Washington Union Stationbus bus
    2. Fly from Ronald Reagan Washington National Airport (DCA) to Westchester County Airport (HPN)plane plane DCA - HPN
    4h 3m
    $158–749

  2. Drive  252.3 mi

    cheapest
    1. Drive from Annapolis to Westportcar car 252.3 mi
    4h 55m
    $46–67

  3. Bus, train

    1. Take the bus from West St & Church Cir to Patapsco Light Rail Station Bay 3bus bus 70
    2. Take the train from Baltimore Penn Station to Stamford Amtrak Stationtrain train Acela
    7h 47m
    $57–144

  4. Bus

    1. Take the bus from Annapolis to New Yorkbus bus FlixBus 2601
    2. Take the bus from Port Authority Bus Terminal to Bridgeport Bus Stopbus bus Greyhound US0255s
    8h 18m
    $52–81

  5. Bus, fly to Laguardia Airport, train

    1. Take the bus from Annapolis to Washington Union Stationbus bus
    2. Fly from Ronald Reagan Washington National Airport (DCA) to Laguardia Airport (LGA)plane plane DCA - LGA
    3. Take the train from 125th Street - Harlem to Darientrain train
    6h 39m
    $115–745

  6. Bus, fly to John F. Kennedy International Airport, train

    1. Take the bus from Annapolis to Washington Union Stationbus bus
    2. Fly from Ronald Reagan Washington National Airport (DCA) to John F. Kennedy International Airport (JFK)plane plane DCA - JFK
    3. Take the train from Grand Central Terminal to Darientrain train
    6h 43m
    $937–1,656

  7. Train (Amtrak)

    1. Take the train from Baltimore Penn Station to Ny Moynihan Train Hall At Penn Stationtrain train Acela
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Bridgeport Amtrak Stationtrain train Northeast Regional / ...
    7h 57m
    $65–156

Annapolis to Westport by bus, tram, foot, and train

Calendar103Weekly Services
Duration7h 47mAverage Duration
Ticket$57Cheapest Price
See schedules

Comparing Your Travel Options

Map of how to get from Annapolis to Westport.ExpandLaunch map view
  • Distance: 292.7 mi
  • Duration: 4h 3m

What companies run services between Annapolis, MD, USA and Westport, CT, USA?

You can take a bus from Annapolis to Post Rd. West at Myrtle Ave. via New York, W 34 St/12 Av, W 34 St/10 Av, Port Authority Bus Terminal, and Bridgeport Transportation Center in around 8h 18m. Alternatively, you can take a bus from COLLEGE AVE & BLADEN ST eb to Post Rd. West at Myrtle Ave. via Cromwell Light Rail Station Bay 1, Glen Burnie, Mt. Royal / MICA, Baltimore Penn Station, Ny Moynihan Train Hall At Penn Station, Bridgeport Amtrak Station, and Water St. at John St. in around 7h 57m.

Airlines
Train operators
Bus 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

Booking & Getting There