Holiday Shopping in and around Chestertown

The holidays are here again… and you know what that means! Shopping!

Don’t strain your eyes pouring over websites. Avoid the stress of the malls and shopping centers. Instead, support local vendors and give your friends and family unique, heartfelt gifts from Chestertown.

Here are some of our favorite shops in and around Chestertown:

Bloomin’ Wild

Bloomin’ Wild is not your typical florist. In addition to beautiful arrangements, they offer an incredible selection of gifts including home and garden items, as well as their own line of soaps, puppets and chocolate.


Chester River Wine & Cheese Co.

You’ll be sure to find gifts for your favorite foodies in this gourmet specialty food market. Chester River Wine & Cheese Co. offers a diverse selection of international and domestic wines & spirits, cut-to-order cheese, charcuterie and pate, handmade jam, mustard, salts and sweets, olive oils and vinegars, and locally raised pork and beef.

Welcome Home

Welcome Home is an extension of gourmet store, Chester River Wine & Cheese Co. From kitchen basics to tableware to beds and linens, you’ll find everything you need to complete your home!



Find something for the book lover in your life. Bookplate is a used bookstore offering a wide range of books from World history to politics to art, architecture, and design to poetry to cooking to gardening. They also have a strong collection of the history and literature from Maryland’s Eastern Shore.

The Finishing Touch

The Finishing Touch is the perfect place for any artist or art lover! They specialize in custom framing, fine art, artist’s materials, digital imaging, art reproduction, and more.

What are your favorite places to visit?