Romantic Things to Do in Chestertown, Maryland

Located on the quaint Eastern Shore of Maryland, Chestertown sits in Kent County and has a population of 5,000 people. Chestertown is teeming with romance and features hundreds of historical homes. The rich history and small town feel of Chestertown makes it a great place to visit with your sweetheart. Here are some of the most romantic things to do in Chestertown, Maryland.

The Mainstay

If you and your date are into music, The Mainstay is the place to be to hear jazz and blues in a comfortable, low-key setting. The venue is decked out with mismatched chairs positioned close to the performers for an intimate musical experience.

Artists’ Gallery

For artistic couples, what better way to spend the day than wandering hand-in-hand through an art gallery? All of the art is beautifully created by local artists. Displays feature jewelry, ceramics, and more.

Blue Crab Chesapeake Charters

If you want a classic romantic experience, go sailing at sunset on the Chesapeake Bay. This local tour company will steer the boat while you and your date take in the sights.

Prince Theatre

If you want to catch a show while visiting Chestertown, bring your loved one to the Prince Theatre. Here you can see the best musical and theatrical talent in Kent County!

Twigs and Teacups

If you are up for a bit of shopping while strolling through Chestertown, you and your date should check out Twigs and Teacups. It’s a cute little gift shop featuring ceramics, soaps, and linens.

Brampton Bed and Breakfast

You can’t get much more romantic than a bed and breakfast. Brampton Bed and Breakfast Inn is one of the top places to stay in Chestertown. After you do a little sight-seeing, you and your sweetheart can spend a cozy evening together at Brampton.

Cassinelli Distilling

Take a stroll down High Street and taste wine, vodka, and gin at the new Chestertown location. It’s small but you and your date will have a great time sampling the best from Cassinelli’s stills.

No matter how you and your partner decide to spend your visit, Chestertown provides a historical and romantic setting for an amazing date.

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