Your Complete Chestertown, Maryland, Holiday Gift Guide

The holidays are quickly approaching! You know what that means: Seemingly endless shopping lists. What if we told you that the perfect presents for everyone on your list can be found right here in Chestertown, Maryland? There’s no better place to spend a relaxing and rejuvenating winter retreat. Why not knock out two birds with one stone and get all of your Christmas shopping done, too? Below is your complete Chestertown, Maryland, holiday gift guide!

Your Local Chestertown, Maryland, Holiday Gift Guide

Bad Alfred’s Distilling

323 High Street, Chestertown

Bad Alfred’s is a working distillery, brewpub and wood-fired grill. Their historic downtown Chestertown building is open for tastings and tours. This spot also boasts three meeting spaces for events or private dinners! We recommend gifting any of their handcrafted spirits. These range between $25—$35 and make incredible, unique gifts.


112 South Cross Street, Chestertown

One of the best places to shop local on the Eastern Shore of Maryland is Bookplate! This adorable spot features a wide and varied selection of new and used books. Here, you’ll also find imported Spanish and Portuguese pottery, so this is an incredible place to create a DIY gift bag. Select one of Bookplate’s signature tote bags (for just $8.00!) featuring the work of local artists and fill it up.


113 South Cross Street, Chestertown

Both local and national artists enjoy representation at Chestertown’s own CREATE, a place that prides itself on all things art, craft, and design! There’s no better gift to give than a colorful Thomas Marrinson pottery piece, and they are plentiful at CREATE. Prices range between $160 and $280.

Crow Vineyard and Winery

12441 Vansant Corner Road, Kennedyville

Just 10 minutes away from Brampton Inn, you’ll discover Crow Vineyard and Winery. Be sure to visit the tasting room for a variety of award-winning dry wines. There’s nothing better than sipping while you shop local! Take home a local gift package featuring Vidal Blanc or Barbera wine, Barbera Eve’s cheese, grass-fed Angus beef, an insulated tote, a Crow t-shirt or sweatshirt, a bag of Crow Coffee, a customized mug, and a branded corkscrew. This package is valued between $75 and $125!

Empty Hangers

114 South Cross Street, Chestertown

Empty Hangers is a boutique consignment shop located in the heart of downtown Chestertown. Their mission is to sell name-brand clothing in excellent condition at affordable prices. Head on in to pick up an impressive, local gift for everyone on your list (without breaking the bank)!

Houston’s Dockside Emporium

315 High Street (#101), Chestertown

Houston’s Dockside Emporium has been a Chestertown staple for over 29 years! They specialize in ladies’ clothing, but feature a fantastic selection of men’s clothing, children’s items, accessories, gifts, books, and much more. We recommend gifting their initial throw (The Mud Pie brand). It retails for $49.

Massoni Art

203 High Street (#2), Chestertown

Massoni Art is one of the Mid-Atlantic’s finest galleries! For over 30 years, this spot has supplied downtown Chestertown with specialty pieces created by brilliant nationally and internationally respected artists. Carla Massoni welcomes you to visit and enjoy the holiday exhibition!

Mimi’s Closet

307 High Street, Chestertown

At Mimi’s Closet, you’ll discover an exciting variety of fashion and gift ideas. The best part? The dedicated staff at Mimi’s will help you score an unforgettable gift for the lovely ladies in your life. Choose Mimi’s cashmere “topper,” a favorite gift choice that comes in 60 luscious colors! Purchase one of these outfit essentials for just $139.

She She on High

321 High Street, Chestertown

She She on High is one of downtown Chestertown’s best local shops. Here, soak in vibrant sights of painted furniture, decor, vintage clothing, and unique gift items. Stop by and greet Gus and Tallulah, the store’s resident piggies! This is a great option for satisfying everyone on your list and conforming to a variety of budgets.

Twigs and Teacups

111 South Cross Street, Chestertown

Twigs and Teacups is a downtown Chestertown boutique that’s dedicated to the art of giving. Come on in and enjoy an eclectic assortment of items perfect for every one of your favorite recipients. You’ll find that even those hardest to shop for will love what you get them from Twigs and Teacups! Popular gifts here such as soaps, socks, and candles range from $3.50 to $14.50.

Welcome Home

107 S Cross Street, Chestertown

Welcome Home carries the tools you need to create amazing meals, wonderful memories, and a restful home. They have the perfect gifts for everyone to make their house a home and offer an assortment of prices!

End a Day of Productive Gift Shopping at Brampton Inn!Fairlee cottage at Brampton Inn with a King bed and seating area for two

After a day filled with fun and fancy-free finds, come back to comfort and hospitality at Brampton Inn! Whether you’re searching for holiday happenings around Chestertown or to continue an existing tradition, Brampton Inn is your perfect home-away-from-home. The Eastern Shore of Maryland isn’t called “The Land of Pleasant Living” for nothing! Our area is characterized by beautiful country roads, unique shops, plenty of rich history, and delicious coastal cuisine. The holidays here make the atmosphere even more magical! No matter what brings you to the Eastern Shore, you’ll love relaxing in your bright, airy, and spacious accommodation at Brampton Inn. The holidays are the best time to experience our gorgeous grounds, fun events (like the Holiday High Tea), and premium amenities!

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