Posted in Maryland Attractions, Shopping, Shops & Boutiques December 22, 2022 by

This Walkable Stretch Of Shops And Restaurants In Small-Town Maryland Is The Perfect Day Trip Destination

Small town charm is abundant in the state of Maryland, especially when it comes to the following area. This waterside town is home to dozens of amazing shops and restaurants, making for a lovely day trip or weekend getaway. Read on for the details and keep this town in mind for a Maryland adventure to remember.

Today we're exploring Chestertown, Maryland, which is located in Kent County.
Google Maps
This waterside town is full of charm, especially when it comes to...
Ivan West / Google
...the downtown area. This area is full of shops and boutiques, restaurants, and more.
Main Street Chestertown / Facebook
The stores sell a variety of items, from antiques, to books, to clothing, and more.
Prawet J / TripAdvisor
Many of the local restaurants are highly-rated. Throughout town you'll find upscale dishes, elevated pub fare, sandwiches... and the list goes on.
Phil W / Google
While exploring the area, be sure to also stop by Fountain Park. This small green space is home to one of the most stunning fountains in Maryland. Have a seat on a bench and enjoy watching (and listening to) the trickling water.
While exploring the area, don't forget to also stop by Fountain Park. This teeny green space is home to one of the most stunning fountains in the state of Maryland.
Ivan West / Google
Chestertown is also home to a marvelous farmers market as well as great community events.
Chestertown Farmers' Market / Facebook
Speaking of events, the annual Wizard-themed festival is a must-see in person at least once.
Chestertown Harry Potter Fans / Facebook
Need a place to stay while exploring Chestertown? No worries -- the town is home to plenty of historic inns and bed & breakfasts.
Management / TripAdvisor
Learn about Chestertown's downtown area by clicking on the website (or Facebook page) linked below. Small town charm awaits!
Downtown Chestertown Association / Facebook

Learn more about Chestertown, including the local businesses, events, and more. You can also follow Main Street Chestertown on Facebook.

Speaking of downtown areas to visit, check out these charming small towns in Maryland!

Address: Chestertown, MD 21620, USA

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