What is the cheapest way to get from Boston to Chestertown?

The cheapest way to get from Boston to Chestertown is to drive which costs $65 - $100 and takes 7h 6m.

What is the fastest way to get from Boston to Chestertown?

The fastest way to get from Boston to Chestertown is to fly and bus and taxi which takes 3h 59m and costs $250 - $550.

How far is it from Boston to Chestertown?

The distance between Boston and Chestertown is 435 miles. The road distance is 378.4 miles.

How do I travel from Boston to Chestertown without a car?

The best way to get from Boston to Chestertown without a car is to train and taxi which takes 8h 27m and costs $170 - $550.

How long does it take to get from Boston to Chestertown?

It takes approximately 3h 59m to get from Boston to Chestertown, including transfers.

Can I drive from Boston to Chestertown?

Yes, the driving distance between Boston to Chestertown is 378 miles. It takes approximately 7h 6m to drive from Boston to Chestertown.

Where can I stay near Chestertown?

There are 22+ hotels available in Chestertown.

Boston to Chestertown - 9 ways to travel via train, plane, bus, taxi, and car

There are 9 ways to get from Boston to Chestertown by plane, bus, taxi, 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.

Fly Boston Logan Airport to Baltimore-Washington International Airport, bus, taxi
best
1. Fly from Boston Logan Airport (BOS) to Baltimore-Washington International Airport (BWI)BOS - BWI
2. Take the bus from BWI-Thurgood Marshall Airport to Kent Island, MD
3. Take the taxi from Kent Island, MD to Chestertown
3h 59m
$259–540
Drive 376.2 mi
cheapest
1. Drive from Boston to Chestertown376.2 mi
7h 6m
$69–100
Train, taxi
1. Take the train from Boston to Aberdeen Amtrak StationNortheast Regional
2. Take the taxi from Aberdeen Amtrak Station to Chestertown
8h 27m
$174–527
Bus, taxi
1. Take the bus from Boston to New York Midtown
2. Take the bus from Midtown - 400 8th Ave to Smyrna, DE - 134 N Dupont Blvd
3. Take the taxi from Smyrna, DE - 134 N Dupont Blvd to Chestertown
8h 40m
$157–233
Fly Boston Logan Airport to Philadelphia International Airport, train, taxi
1. Fly from Boston Logan Airport (BOS) to Philadelphia International Airport (PHL)BOS - PHL
2. Take the train from 30th Street Station to Aberdeen Amtrak Station
3. Take the taxi from Aberdeen Amtrak Station to Chestertown
5h 22m
$225–727
Fly Boston Logan Airport to Ronald Reagan Washington National Airport, train, drive
1. Fly from Boston Logan Airport (BOS) to Ronald Reagan Washington National Airport (DCA)BOS - DCA
2. Take the train from Washington Union Station to Edgewood
3. Drive from Edgewood to Chestertown
6h 21m
$124–707
Bus to Manchester Airport, fly to Baltimore-Washington International Airport, bus, taxi
1. Take the bus from Boston to Boston Manchester Airport
2. Fly from Manchester Airport (MHT) to Baltimore-Washington International Airport (BWI)MHT - BWI
3. Take the bus from BWI-Thurgood Marshall Airport to Kent Island, MD
4. Take the taxi from Kent Island, MD to Chestertown
6h 4m
$219–618
Train, taxi via New York
1. Take the train from Boston to Ny Moynihan Train Hall At Penn Station
2. Take the train from Ny Moynihan Train Hall At Penn Station to Aberdeen Amtrak Station
3. Take the taxi from Aberdeen Amtrak Station to Chestertown
8h 31m
$173–1,124
Bus, drive
1. Take the bus from South Station to Port Authority Bus Terminal
2. Take the bus from Port Authority Bus Terminal to White Marsh Park & Ride
3. Drive from White Marsh Park & Ride to Chestertown
9h 57m
$73–152

Boston Logan Airport (BOS) to Baltimore-Washington International Airport (BWI) flights

52Weekly Planes

1h 40mAverage Duration

$52Cheapest Price

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Questions & Answers

Map of how to get from Boston to Chestertown.

Launch map view

Distance: 432.9 mi
Duration: 3h 59m

What companies run services between Boston, MA, USA and Chestertown, MD, USA?

There is no direct connection from Boston to Chestertown. However, you can fly to Baltimore-Washington International Airport (BWI), walk to BWI-Thurgood Marshall Airport, take the bus to Kent Island, MD, then take the taxi to Chestertown. Alternatively, you can take the train to Aberdeen Amtrak Station then take the taxi to Chestertown.

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