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Visiting Chestertown, MD


With a colonial history dating back to the 17th century, Chestertown, Maryland is proud of its maritime heritage. Sitting on the banks of the Chester River, sailing ships can still be seen coming into port. The city is the home of the Schooner Sultana, an exact replica of an 18th century ship that served in the British Royal Navy, now operating as an educational vessel. Every Memorial Day, the city hosts The Chestertown Tea Party Festival, proudly tossing the British overboard annually.
Flights: Cheap airfare to Chestertown (arriving in Baltimore, MD - Balt./Wash. International Airport)

Traveler Advice on Chestertown

11 Hotels & Accommodations

1 Thing to Do

10 Restaurants

Before You Go

  • Traveler Articles – Advice from real travelers

Weather

 | 
Monthly Averages
Month
High
Low
Jul
80°F 26°C
68°F 20°C
Aug
79°F 26°C
68°F 20°C
Sep
71°F 21°C
59°F 15°C
Oct
60°F 15°C
49°F 9°C
Nov
50°F 10°C
39°F 3°C
Dec
43°F 6°C
33°F 0°C
Extended Forecast
Saturday
Jul 18
Hi:
83°F 28°C
Lo:
63°F 17°C
Sunday
Jul 19
Hi:
81°F 27°C
Lo:
63°F 17°C
Monday
Jul 20
Hi:
81°F 27°C
Lo:
65°F 18°C

Traveler Reviews

Brooks Tavern in the Radcliffe Mill

5 of 5 stars
maddief
Jul 16, 2009

After being turned away for coming too late on a summer weekend, we reluctantly decided to give the Tavern another try. Thank goodness we did -- it's the best food I've had since my last trip to...more

Holiday Inn Express Hotel & Suites Chestertown

5 of 5 stars
Washington, DC
Jul 13, 2009

This hotel has all the essentials of a great hotel. Its clean, quiet, everything works, the bed and pillows are very comfortable, the staff friendly and helpful, a good breakfast, nice sized rooms,...more

Comfort Suites

4 of 5 stars
Webster, NY
Jul 12, 2009

Everyone was friendly at the front desk. The rooms was spacious and clean. The breakfast room was clean. more

Chestertown Forum

Ask a Question or Browse the Discussions
Sea Glass Hunt for a few hours? October 20, 2008, 5 replies
Anything doing on Halloween weekend? October 14, 2008, 2 replies
Kennedyville Inn is the best place September 26, 2008, 1 reply
The Brampton Inn and Fun in Chestertown September 26, 2008, no replies
accomodations. November 14, 2007, 2 replies
What to do in Chestertown in January? September 21, 2007, 2 replies
Totally Disagree April 16, 2007, 1 reply
Worst place January 10, 2007, 7 replies
Relaxing, romantic vacation - where to go? today, no replies
jet skiing July 15, 2009, 1 reply
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