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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.

Traveller Advice on Chestertown

11 Hotels & Accommodations

1 Thing to Do

10 Restaurants

Before You Go

  • Traveller Articles – Advice from real travellers

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
9 Nov
Hi:
67°F 19°C
Lo:
47°F 8°C
Tuesday
10 Nov
Hi:
63°F 17°C
Lo:
45°F 7°C
Wednesday
11 Nov
Hi:
50°F 10°C
Lo:
34°F 1°C

Reviews you can trust

Brampton Bed & Breakfast Inn

5 of 5 stars
Washington, DC
8 Nov 2009

My husband and I stayed at Brampton Inn for an anniversary getaway weekend and couldn't have been more delighted with the experience. The rooms were lovely, with generous amenities like cozy robes, a...more

Brampton Bed & Breakfast Inn

5 of 5 stars
new jersey
8 Nov 2009

My husband and I, along with my sister and her husband, just returned from a 3-night stay at the Brampton Inn in Maryland. We were celebrating our wedding anniversaries together. As soon as we...more

Blue Heron Cafe and Inn

4 of 5 stars
Rising Sun, IN
7 Nov 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

Chestertown Forum

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