There are 7 ways to get from Chestertown to Boston by taxi, train, bus, car, or plane
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Taxi, train (Amtrak)
best- Take the taxi from Chestertown to Aberdeen Amtrak Stationtaxi
- Take the train from Aberdeen Amtrak Station to Bostontrain Northeast Regional
8h 14m$226–419Drive 375.4 mi
cheapest- Drive from Chestertown to Bostoncar 375.4 mi
7h 10m$69–99Taxi, bus
- Take the taxi from Chestertown to Smyrna, DE - 134 N Dupont Blvdtaxi
- Take the bus from Smyrna, DE - 134 N Dupont Blvd to Midtown - 400 8th Avebus
- Take the bus from New York Midtown to Bostonbus
8h 34m$187–245Taxi, bus, fly to Manchester Airport
- Take the taxi from Chestertown to Kent Islandtaxi
- Take the bus from Kent Island to Baltimorebus
- Fly from Baltimore-Washington International Airport (BWI) to Manchester Airport (MHT)plane BWI - MHT
- Take the bus from Boston Manchester Airport to Bostonbus
6h 10m$195–608Drive, bus
- Drive from Chestertown to Baltimorecar
- Take the bus from Baltimore to New Yorkbus
- Take the bus from New York to Bostonbus
10h 19m$99–175Taxi, bus, fly to Theodore Francis Green State Airport, train
- Take the taxi from Chestertown to Kent Islandtaxi
- Take the bus from Kent Island to Baltimorebus
- Fly from Baltimore-Washington International Airport (BWI) to Theodore Francis Green State Airport (PVD)plane BWI - PVD
- Take the train from TF Green Airport to South Stationtrain
6h 16m$181–531Taxi, bus, fly to Bradley International Airport
- Take the taxi from Chestertown to Kent Islandtaxi
- Take the bus from Kent Island to Baltimorebus
- Fly from Baltimore-Washington International Airport (BWI) to Bradley International Airport (BDL)plane BWI - BDL
- Take the bus from Hartford Union Station to Bostonbus
7h 5m$213–715
Baltimore-Washington International Airport (BWI) to Manchester Airport (MHT) flights
Comparing Your Travel Options
The cheapest way to get from Chestertown to Boston is to drive which costs $65 - $100 and takes 7h 10m.
The fastest way to get from Chestertown to Boston is to taxi and bus and fly which takes 6h 10m and costs $190 - $650.
The distance between Chestertown and Boston is 444 miles. The road distance is 377.6 miles.
The best way to get from Chestertown to Boston without a car is to taxi and train which takes 8h 14m and costs $220 - $420.
It takes approximately 8h 14m to get from Chestertown to Boston, including transfers.
Yes, the driving distance between Chestertown to Boston is 378 miles. It takes approximately 7h 10m to drive from Chestertown to Boston.
There are 1765+ hotels available in Boston.
What companies run services between Chestertown, MD, USA and Boston, MA, USA?
There is no direct connection from Chestertown to Boston. However, you can take the taxi to Aberdeen Amtrak Station then take the train to Boston. Alternatively, you can take the taxi to Smyrna, DE - 134 N Dupont Blvd, take the bus to Midtown - 400 8th Ave, walk to New York Midtown, then take the bus to Boston.
- Website
- southwest.com
Flights from Baltimore-Washington International Airport to Manchester Airport
- Ave. Duration
- 1h 25m
- When
- Every day
- Estimated price
- $60–400
Flights from Baltimore-Washington International Airport to Theodore Francis Green State Airport
- Ave. Duration
- 1h 21m
- When
- Every day
- Estimated price
- $45–320
Flights from Baltimore-Washington International Airport to Bradley International Airport
- Ave. Duration
- 1h 16m
- When
- Every day
- Estimated price
- $70–490
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Aberdeen Amtrak Station to Boston
- Ave. Duration
- 6h 54m
- Frequency
- 5 times a week
- Estimated price
- $100–270
- Website
- Amtrak
Train from TF Green Airport to South Station
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $9–16
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $9–16
- climing44@yahoo.com
- Website
- Rockledge Bus
Bus from Smyrna, DE - 134 N Dupont Blvd to Midtown - 400 8th Ave
- Ave. Duration
- 2h 30m
- Frequency
- Once daily
- Estimated price
- $30–45
- Website
- Rockledge Bus
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from New York Midtown to Boston
- Ave. Duration
- 4h 20m
- Frequency
- Every 2 hours
- Estimated price
- $30–50
- Schedules at
- Flixbus USA
Bus from Hartford Union Station to Boston
- Ave. Duration
- 1h 55m
- Frequency
- Twice daily
- Estimated price
- $15–23
- Schedules at
- Flixbus USA
- Phone
- +1 410-912-6000
- reservations@bayrunnershuttle.com
- Website
- BayRunner Shuttle
Bus from Kent Island to Baltimore
- Ave. Duration
- 35 min
- Frequency
- Every 4 hours
- Estimated price
- $55–110
- Schedules at
- BayRunner Shuttle
Bus from Kent Island to Baltimore
- Ave. Duration
- 35 min
- Frequency
- Every 4 hours
- Estimated price
- $55–110
- Schedules at
- BayRunner Shuttle
Bus from Kent Island to Baltimore
- Ave. Duration
- 35 min
- Frequency
- Every 4 hours
- Estimated price
- $55–110
- Schedules at
- BayRunner Shuttle
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- Greyhound
Bus from Boston Manchester Airport to Boston
- Ave. Duration
- 1h 30m
- Frequency
- Twice daily
- Estimated price
- $8–13
- Website
- Greyhound
Bus from Hartford Union Station to Boston
- Ave. Duration
- 1h 45m
- Frequency
- Every 2 hours
- Estimated price
- $16–26
- Website
- Greyhound
- Phone
- 1-800-343-9999
- Website
- Peter Pan
Bus from Baltimore to New York
- Ave. Duration
- 3h 10m
- Frequency
- Hourly
- Estimated price
- $45–80
- Website
- Peter Pan
Bus from New York to Boston
- Ave. Duration
- 4h 35m
- Frequency
- Hourly
- Estimated price
- $40–75
- Website
- Peter Pan
- Ave. Duration
- 49 min
- Estimated price
- $70–150
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