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

The cheapest way to get from Bridgeport to Chestertown is to drive which costs $40 - $60 and takes 4h 22m.

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

The fastest way to get from Bridgeport to Chestertown is to drive which takes 4h 22m and costs $40 - $60.

How far is it from Bridgeport to Chestertown?

The distance between Bridgeport and Chestertown is 270 miles. The road distance is 225.8 miles.

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

The best way to get from Bridgeport to Chestertown without a car is to train and taxi which takes 5h 23m and costs $150 - $440.

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

It takes approximately 5h 23m to get from Bridgeport to Chestertown, including transfers.

Can I drive from Bridgeport to Chestertown?

Yes, the driving distance between Bridgeport to Chestertown is 226 miles. It takes approximately 4h 22m to drive from Bridgeport to Chestertown.

Where can I stay near Chestertown?

There are 22+ hotels available in Chestertown.

Bridgeport to Chestertown - 4 ways to travel via train, taxi, bus, and car

There are 4 ways to get from Bridgeport to Chestertown by train, taxi, bus, 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.

Train, taxi
best
1. Take the train from Bridgeport Amtrak Station to Aberdeen Amtrak StationNortheast Regional
2. Take the taxi from Aberdeen Amtrak Station to Chestertown
5h 23m
$150–438
Drive 224.5 mi
cheapest
1. Drive from Bridgeport to Chestertown224.5 mi
4h 22m
$41–60
Train, bus, taxi
1. Take the train from Bridgeport to Grand Central Terminal
2. Take the bus from New York, Chinatown-152 East Broadway to Smyrna, DE - 134 N Dupont Blvd
3. Take the taxi from Smyrna, DE - 134 N Dupont Blvd to Chestertown
6h 55m
$140–218
Bus, drive
1. Take the bus from Bridgeport Bus Stop 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
7h 40m
$56–133

Questions & Answers

Launch map view

Distance: 268.3 mi
Duration: 5h 23m

What companies run services between Bridgeport, CT, USA and Chestertown, MD, USA?

There is no direct connection from Bridgeport to Chestertown. However, you can take the train to Aberdeen Amtrak Station then take the taxi to Chestertown. Alternatively, you can take the train to Grand Central Terminal, walk to 42 St-Bryant Park, take the subway to East Broadway, walk to New York, Chinatown-152 East Broadway, take the bus to Smyrna, DE - 134 N Dupont Blvd, then take the taxi to Chestertown.

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