Chesapeake Charm

An independent spirit and loads of local color make Chestertown, Maryland, one of our all-time-favorite small towns.
Chesapeake Charm

The Heart of Chestertown

The Imperial Hotel, at only 105 years old, is a relative newcomer. Its Front Room Restaurant and Lounge keep locals returning for a sophisticated evening meal, casual lunch, or Sunday brunch. The dozen upstairs lodging rooms provide a quaint and comfy spot for guests.

In the mornings the busiest spot is Play It Again Sam coffee shop. Tables and chairs spill outdoors for patrons who bring their dogs along. Inside, conversations drift between tables as friends greet one another. It takes barely a minute before someone asks me where I’m from and then invites me to join several families at the concert in Fountain Park, which takes place every other Saturday evening.

As I sip my coffee, I plan my day. Check out the farmers market and the shops, seek out the point where the Chester River meets the Bay, and return for a musical sunset with my new friends--the ideal midsummer day in a perfect small town.

"Chesapeake Charm" is from the July 2008 issue of Southern Living. Because prices, dates, and other specifics are subject to change, please check all information to make sure it's still current before making your travel plans.