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Chestertown to Windham bus

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Chestertown - Windham Bus Schedule

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Journey Information

There is one daily bus from Chestertown to Windham. Traveling by bus from Chestertown to Windham usually takes around 7 hours and 50 minutes, but some buses might arrive slightly earlier or later than scheduled depending on traffic conditions.

Distance96 mi (154 km)
Shortest duration7h 50m
Cheapest priceUS$29.00
Most frequent serviceAdirondack Trailways
Bus lines1

What bus companies travel from Chestertown to Windham?

There is one intercity bus company available to search and book on Wanderu that operates from Chestertown to Windham. Adirondack Trailways is the only company that has bus schedules available to search and book at the moment. It only makes the trip once a day on most days.

BusDaily TripsAvg. TimeAvg. Price
Adirondack Trailways17h 51mUS$30.29
  • Part of the nationwide Trailways bus network, Adirondack Trailways serves routes across New York State. Most of its service connects the Adirondacks and Hudson Valley with New York City. On the Chestertown to Windham route, Adirondack Trailways tickets are on average, but you can score a cheaper ticket as low as US$29 if you book well in advance. Buses are comfortable and well-equipped with Wi-Fi, power outlets, restrooms, air conditioning, and reclinable seats with footrests.

Frequently Asked Questions

The bus takes an average of 7 hours and 50 minutes to cover the 154 kilometers from Chestertown to Windham. It’s definitely on the longer side, so plan to get comfortable for a long road trip. Keep in mind that your actual bus may arrive earlier or later than scheduled, depending on whether there is more or less traffic than usual.

With many people traveling in the middle of the week, Wednesday is the busiest day of the week for bus travel. If you are planning to travel on a Wednesday, you should make sure to book tickets well in advance as they may sell out.

On the other hand, Tuesday is typically the least busy day for bus travel on this route. If you’re looking for a little extra space, a Tuesday ticket is the way to go.

There is usually only one bus per day from Chestertown to Windham. It leaves the station in Chestertown at 1:00pm each day. The time might vary for specific dates, so be sure to search on Wanderu for the most up-to-date information.

There is usually only one bus per day from Chestertown to Windham. However, it is not a direct bus, so you will have to get off your original vehicle to change buses during the trip.

City Information

Station Information

Where does the bus leave from in Chestertown?

Main departure station: Main Street

Most buses depart from the main station in Chestertown.

All bus stations in Chestertown:

  • Main Street

Where does the bus arrive in Windham?

Main arrival station: Main St and Church St

All buses from Chestertown arrive at one main station in Windham.

Bus stations in Windham:

  • Main St and Church St

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