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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.
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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
Nov
50°F 10°C
39°F 3°C
Dec
43°F 6°C
33°F 0°C
Jan
37°F 2°C
28°F -2°C
Feb
40°F 4°C
31°F 0°C
Mar
46°F 7°C
34°F 1°C
Apr
59°F 15°C
44°F 6°C
Extended Forecast
Monday
Nov 9
Hi:
65°F 18°C
Lo:
47°F 8°C
Tuesday
Nov 10
Hi:
67°F 19°C
Lo:
45°F 7°C
Wednesday
Nov 11
Hi:
54°F 12°C
Lo:
40°F 4°C

Reviews you can trust

Blue Heron Cafe and Inn

4 of 5 stars
Rising Sun, IN
Nov 7, 2009

Nice atmosphere, owner/host not that personable to the 'out-of- towners" like ourselves. Wait staff, although busy and a bit stiff, were sufficeint. The ginger carrot soup was a melody that exploded...more

The Imperial Hotel and Restaurant

4 of 5 stars
Rising Sun, IN
Nov 7, 2009

The Imperial Hotel in Chestertown is a wonderful old jem! We stayed in the third floor suite which is very spacious, and has an old shabby chicness to it. The bedroom and bathroom are spacious and...more

The Fish Whistle

Nov 2, 2009
0/1 found this review helpful

We had the Crab Imperial & Salad Special during the Downrigging weekend. The food was very good, however, our server was rather unpleasant. We asked for a window table & was willing to wait for one,...more

Chestertown Forum

Ask a Question or Browse the Discussions
Great Oak Manor November 03, 2009, no replies
seaglass October 22, 2009, 3 replies
Avoid this cottage September 28, 2009, no replies
Eastern Shore November 07, 2009, 8 replies
airport transportation November 06, 2009, 3 replies
Where to Stay October 04, 2009, 2 replies
Fun All-You-Can Eat Crab Shack Suggestions October 02, 2009, 34 replies
crab shack September 28, 2009, 2 replies
Eating along i-68, Cumberland and West September 25, 2009, 1 reply
Chesapeake Bay Suggestions September 24, 2009, 2 replies
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