Best of Chestertown, MD
The best restaurants, cafés, bars, shops and things to do in Chestertown, MD — mapped and organized by category.
About Chestertown
Chestertown serves as the county seat of Kent County, which holds the distinction of being the oldest county in Maryland. The town had a population of 5,532 according to the 2020 census.
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Phat Daddy’s BBQ Shack
Phat Daddy’s BBQ Shack is a barbecue restaurant located in the Reba L Anthony Estates neighborhood.
View details →Best Hotels in Chestertown
5 places · Where to stay, from budget-friendly to boutique.
Best Restaurants in Chestertown
4 places · Where to eat, from neighborhood staples to standout kitchens.
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Phat Daddy’s BBQ Shack
Phat Daddy’s BBQ Shack is a barbecue restaurant located in the Reba L Anthony Estates neighborhood.
Best Things to Do in Chestertown
2 places · Museums, landmarks and the experiences worth your time.
Best Shops in Chestertown
1 places · Independent boutiques, bookstores and places to browse.
Best Parks & Outdoors in Chestertown
11 places · Green space, gardens and room to breathe.
Nearby cities to explore
More guides within driving distance of Chestertown.
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- Edgemere, MD 22 places
- Aberdeen, MD 65 places
- Essex, MD 71 places
- Cape Saint Claire, MD 5 places
- Dundalk, MD 203 places
- Bel Air South, MD 38 places
- Middletown, DE 32 places