We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Best of Chestertown Guide

Print this guide 
Chestertown
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.

All things to do » Things to do

Historical Society of Kent County
Historical Society of Kent County
Owner description: Visit the Geddes-Piper House, a beautiful 1783 merchant's home that provides an overview of Kent Co history from first settlement to the 20th century. Period furniture, porcelain... more Owner description: Visit the Geddes-Piper House, a beautiful 1783 merchant's home that provides an overview of Kent Co history from first settlement to the 20th century. Period furniture, porcelain and textiles offer the perfect backdrop for the story of the region, conveyed through interpretive signage. Our Genealogy & Local History Library contains a full collection of maps, cemetery records and reference books. less
Attraction type: Museums; History museums
See nearby places to eat
Carla Massoni Gallery
Carla Massoni Gallery
Attraction type: Landmarks & points of interest
See nearby places to eat

Additional nearby recommended attractions:

Ripken Stadium
Ripken Stadium(Aberdeen)
Attraction type: Arenas & stadiums
See nearby places to eat
Terrapin Nature Park
Terrapin Nature Park(Stevensville)
Attraction type: Parks; Hiking trails
See nearby places to eat
Chesapeake Exploration Center
Chesapeake Exploration Center(Chester)
Attraction type: Visitor centers
See nearby places to eat

All places to eat » Places to eat

Lemon Leaf Cafe
Lemon Leaf Cafe
Ranked #1 of 34 Restaurants in Chestertown
Cuisines: American
Dining options: Breakfast/Brunch, Reservations, Late Night
LUISA'S cucina italiana
LUISA'S cucina italiana
Ranked #2 of 34 Restaurants in Chestertown
Price: $7 - $25
Cuisines: Italian, Seafood
Good for: Families with children, Romance, Doing business, Special occasions, Entertaining clients, Dining on a budget
Dining options: Lunch, Dinner, Reservations, Delivery, Dessert
No photo provided
Procolino's Pizza
Ranked #3 of 34 Restaurants in Chestertown
Price: $5 - $10
Cuisines: Italian
Blue Heron Cafe and Inn
Blue Heron Cafe and Inn
Ranked #4 of 34 Restaurants in Chestertown
Dining options: Dinner, Reservations
Herb's Soups and Such
Herb's Soups and Such
Ranked #5 of 34 Restaurants in Chestertown

All accommodations » Where to stay - Budget

No photo provided
Widow's Walk Inn
$30 - $135
Ranked #4 of 12 Chestertown B&B and Inns
White Swan Tavern
White Swan Tavern
$30 - $180
Ranked #7 of 12 Chestertown B&B and Inns

Additional nearby recommended accommodations:

Mariners Motel
2.0 of 5
Mariners Motel
$87 - $94
Ranked #1 of 3 Hotels in Rock Hall
Show Prices

All accommodations » Where to stay - Midrange

Simply Bed and Bread
Simply Bed and Bread
$99 - $139
Ranked #1 of 12 Chestertown B&B and Inns
The Inn at Mitchell House
The Inn at Mitchell House
$109 - $239
Ranked #3 of 12 Chestertown B&B and Inns
Holiday Inn Express Hotel & Suites Chestertown
2.5 of 5
Holiday Inn Express Hotel & Suites Chestertown
$104 - $179
Ranked #1 of 2 Hotels in Chestertown
Show Prices

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.