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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

9 Restaurants

Before You Go

  • Traveler Articles – Advice from real travelers

Weather

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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
Sunday
Nov 22
Hi:
56°F 13°C
Lo:
41°F 5°C
Monday
Nov 23
Hi:
54°F 12°C
Lo:
43°F 6°C
Tuesday
Nov 24
Hi:
58°F 14°C
Lo:
43°F 6°C

Reviews you can trust

Brampton Bed & Breakfast Inn

Nov 19, 2009

We decided to take a little two night mid-week mini-vacation at Brampton before picking up our daughter at nearby Washington College. The Inn did not disappoint. There are various teas, soda and...more

Brampton Bed & Breakfast Inn

4 of 5 stars
New York
Nov 18, 2009

We spent a weekend at the Brampton Inn and had a wonderful time. The accomodations were first class, breakfast and tea were delicious and the ammenities (complimentary beer, wine, soda, beverages,...more

Brampton Bed & Breakfast Inn

5 of 5 stars
Baltimore, MD
Nov 13, 2009

My husband and I "won" a night at the Brampton Inn through a silent auction for charity, but they were as warm and welcoming as if we were regular guest, offering advice on local activities and...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
Is it free to visit the white house? November 20, 2009, 2 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
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Destinations of the Day
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  • Major features: water sports, beaches, nature tours
  • 24,309 TripAdvisor reviews of 401 accommodations, 368 attractions and 677 restaurants
Culture-seekers will be charmed be La Isla's heritage and history, from Old San Juan's charms to folk art and festivals in the outlying towns.
Algarve, Portugal
  • Resident population: 350,000 Annual visitors: 5,000,000 (est.)
  • Major features: golf courses, beaches
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The Algarve's sunny shores offer perfect escapes for all types, from those seeking the hot nightlife of flashy, energetic Lagos to those desiring secluded stays in rambling Sagres.
Miami Beach, Florida
  • Resident population: 87,925 Annual visitors: 10,000,000 (est.)
  • Major features: nightlife, beaches, shopping, art museums
  • 25,633 TripAdvisor reviews of 355 accommodations, 69 attractions and 399 restaurants
South Beach, or SoBe, is Miami Beach's buzziest bit. The vibrant area, with its pastel-hued buildings, hip nightclubs, trendy shops and see-and-be-seen restaurants, attracts socialites and their satellites year-round.
Dubai, United Arab Emirates
  • Resident population: 1,422,000 Annual visitors: 6,120,000 (est.)
  • Major features: shopping, historic sites, beaches, nightlife, golf courses
  • 15,630 TripAdvisor reviews of 488 accommodations, 71 attractions and 374 restaurants
With its ultramodern skyline, it's easy to forget that Dubai, part of the United Arab Emirates, was once a small town of Bedouin traders.
Benidorm, Spain
  • Resident population: 66,902 Annual visitors: 2,457,000 (est.)
  • Major features: beaches, nightlife, theme parks
  • 9,711 TripAdvisor reviews of 301 accommodations, 16 attractions and 186 restaurants
Bask on four miles of golden beaches, hit the Mediterranean Sea on water skis or stroll along Benidorm's promenade and revel in its seaside charms; it's a true Spanish beauty of the Costa Blanca.