Chestertown (Maryland) Travel Guide — Things to Do, Food & Hotels
town in Maryland, United States
About Chestertown (Maryland)
Chestertown, the county seat of Kent, the Eastern Shore of Marylands's oldest county, was founded in 1706 and served as a port of entry during colonial times. A town rich in history, its attractions include a blend of past and present. Its brick sidewalks and attractive antique stores, restaurants and inns beckon visitors and residents alike to wander through the historic district and enjoy homes and places with architecture ranging from the Georgian mansions of wealthy colonial merchants to the elaborate style of the Victorian era. Chestertown is situated on a scenic peninsula where the Chester and Sassafras rivers meander into Chesapeake Bay.
Where to Eat in Chestertown (Maryland)
Must-try local food and restaurants:
- 🍴Luisa's Cucina Italiana
- 🍴The Front Room at the Imperial Hotel
Where to Stay in Chestertown (Maryland)
- 🏨Brampton Bed and Breakfast Inn
- 🏨Great Oak Manor
- 🏨Holiday Inn Express
Chestertown (Maryland) Travel Guide Sections
Our comprehensive guide covers 10 sections including: