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

River Arts Chestertown
River Arts Chestertown
Owner description: RiverArts Mission: To engage our community in the creation, appreciation, and support of the arts through education, events, and exhibitions. RiverArts Vision: To inspire and... more Owner description: RiverArts Mission: To engage our community in the creation, appreciation, and support of the arts through education, events, and exhibitions. RiverArts Vision: To inspire and foster creativity as a positive and sustainable force that enriches our community and establishes the region as a premier arts destination. less
Attraction type: Educational Sites
See nearby places to eat

Additional nearby recommended attractions:

No photo provided
The Mainstay(Rock Hall)
Attraction type: Performances; Theaters
See nearby places to eat
Ripken Stadium
Ripken Stadium(Aberdeen)
Attraction type: Arenas/ Stadiums/ Fields
See nearby places to eat
Terrapin Nature Park
Terrapin Nature Park(Stevensville)
Attraction type: Parks; Hiking Trails
See nearby places to eat
No photo provided
Chesapeake Bay Environmental Center(Grasonville)
See nearby places to eat

All places to eat » Places to eat

Lemon Leaf Cafe
Lemon Leaf Cafe
Ranked #1 of 32 restaurants in Chestertown
Cuisines: American
Dining options: Breakfast/Brunch, Reservations, Late Night
Evergrain Bread Company
Evergrain Bread Company
Ranked #2 of 32 restaurants in Chestertown
Price:
Cuisines: Bakery
LUISA'S
LUISA'S
Ranked #3 of 32 restaurants in Chestertown
Price: $5 - $25
Cuisines: Italian
Good for: Families with children, Romance, Doing business, Special occasions, Entertaining clients, Dining on a budget
Dining options: Lunch, Dinner, Reservations, Delivery, Dessert
JR's Past-Time Pub
JR's Past-Time Pub
Ranked #4 of 32 restaurants in Chestertown
Price: $7 - $15
Cuisines: Pub
Dining options: Breakfast/Brunch, Reservations, Late Night
Blue Heron Cafe and Inn
Blue Heron Cafe and Inn
Ranked #5 of 32 restaurants in Chestertown
Dining options: Dinner, Reservations

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:

Wingate by Wyndham Aberdeen /Edgewood
2.5 of 5
Wingate by Wyndham Aberdeen /Edgewood
$99 - $137
Ranked #1 of 1 hotels in Belcamp
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 - $199
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.