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.
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Courtyard Inn
Courtyard Inn is a hotel located in the Reba L Anthony Estates neighborhood.
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White Swan Tavern
White Swan Tavern is a hotel located in the Reba L Anthony Estates neighborhood. It offers accommodations for guests visiting the area.
Best Restaurants in Chestertown
4 places · Where to eat, from neighborhood staples to standout kitchens.
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Luisa's Cucina Italiana
Luisa's Cucina Italiana serves Italian dishes in Reba L Anthony Estates.
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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.
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China House
China House is a restaurant serving Chinese cuisine located in the Reba L Anthony Estates neighborhood.
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Procolino's Pizza (Proc’s)
Procolino's Pizza (Proc’s) serves pizza, Italian dishes, pasta, salad and seafood in the Reba L Anthony Estates neighborhood.
Best Things to Do in Chestertown
2 places · Museums, landmarks and the experiences worth your time.
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Chestertown Station
Chestertown Station, a Queen Anne‑style railway station built in 1902–03 for the Pennsylvania Railroad, sits in Chestertown, Kent County, Maryland. The 1½‑story building offers a hip roof and wide bracketed overhang that sheltered passengers on all four sides.
Best Shops in Chestertown
1 places · Independent boutiques, bookstores and places to browse.
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The Bookplate
The Bookplate is a shop located in the Reba L Anthony Estates neighborhood. It offers a selection of books and related items for shoppers in the area.
Best Parks & Outdoors in Chestertown
11 places · Green space, gardens and room to breathe.
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Village At Chestertown Park
Village At Chestertown Park offers green space for strolls and family outings.
Nearby cities to explore
More guides within driving distance of Chestertown.
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