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

Southern Living Editors

I've been exploring Chestertown’s redbrick sidewalks for only an hour, but I’m already mesmerized by its picture-perfect scenes. Streams of yellow sunlight filter through the leafy green canopy, beaming on a tidy row of shops with inviting windows.

I spent last night at The Imperial Hotel--recommended by a friend as a fine retreat--and arose this morning to wander toward the river. There, a tiny flotilla of sailboats gently bobs in the calm water as birds fly overhead. The Sultana, a replica of a historic schooner, sits tied to the dock. In its quiet berth, it looks ready for adventure.

I follow a narrow walk between 18th-century homes. Peeking into the lush gardens, I breathe deeply the heady scents. Dark red roses cascade over the old white picket fences, and sidewalks are littered with soft petals just like a wedding aisle. Over in Fountain Park, the town square, people gather for the Saturday morning farmers market.

An Independent-Minded Place
Beneath the quiet historic exterior, energy buzzes throughout this village that hugs the Chester River. Proud of all the locally owned businesses, they strive to keep Chestertown’s small-town charm. For instance, they refused Wal-Mart moving in, and another time they opposed a proposed bridge across the Bay, hoping to keep out the mainland’s congestion. Consequently, they’ve preserved their village’s authenticity.

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.

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