Explore Chestertown's

Unique Retailers

A Curated Shopping Experience

Chestertown’s small business retail community has a variety of shopping options. Fashionable apparel, fine jewelry, sportswear, collectibles and antiques, eclectic galleries, and so much more can be found. These independently-owned businesses not only create jobs and support our local economy, they are here to cater to customer’s individual needs.

Featured Main Street Retailers

Browse our unique array of boutiques and retailers, you’ll find one-of-a-kind gifts at a variety of Chestertown shops, letting you take home a piece of Maryland’s Eastern Shore.


The Crumpton Auction

Dixon’s Furniture Auction, known by many as the Crumpton Auction, is a third generation auction company established in 1961 by Norman Dixon. They are one of the largest discovery auctions, always on the edge of what’s new in the auction and antique world. You literally never know what you may find.

Chestertown Retailers on Instagram

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