Shops

Chester River Wine & Cheese Co.
Chester River Wine & Cheese Co. is a specialty food market offering international and domestic wine, cut-to-order cheese, onsite wine by the glass, and cheese board service.
443-282-0220
117 South Cross Street
Chestertown, Maryland 21620
Days Open
All
Hours
Tues-Sat 10am-7pm; Sun & Mon 10am-4pm
DCA Member
Houston’s Dockside Emporium
The place to shop on the Eastern Shore for CLASSIC APPAREL FOR WOMEN AND MEN
@houstonsdocksideemporium
410-778-9079
315 High Street Suite 101
Chestertown MD 21620
Days Open
All
Hours
Monday – Saturday 9:30 am – 5:30 pm, Sunday 11 am – 4 pm
DCA Member
Mimi’s Closet
Mimi’s is the boutique with lots of variety. Our staff can help you put a look together for any occasion or you can browse through our great selection of casual or dressy choices. Stop in and say hello. . . We think you’ll enjoy the “Mimi’s Difference”!
443-282-0225
307 High Street
Chestertown MD 21620
Days Open
All
Hours
Mon – Sat 10 am – 5 pm, Sun 11 am – 4 pm
DCA Member
Music Life
Instrument lessons, sales and repair. Students of all ages and any skill level can discover the delight of music and experience the joy of sharing it with others
410-778-7010
241 High Street
Chestertown
Days Open
Mon, Tues, Wed, Thurs, Fri, Sat
Hours
Mon 3-6, Tues-Thurs 10:30-6:30, Fri 10:30-7, Sat 9:30-5
DCA Member
Riverside Unique
Unique handmade gifts made from local Maryland Artisans.
410-778-2073
Business Fax
410-778-2074
227 High Street
Chestertown, MD 21620
Days Open
Mon, Tues, Wed, Thurs, Fri, Sat
Hours
Mon- Fri: 10am – 5pm. Sat 10 am – 2pm
DCA Member
The Bookplate
The Bookplate is an independent bookstore in the heart of downtown Chestertown, MD. We specialize in first editions, regional history, and fiction, but our collection has gradually expanded to include art books, field guides, essays, comics, and beyond. Plus custom, hand painted pottery imported from Portugal and Spain.
410-778-4167
112 S. Cross Street
Chestertown
Days Open
All
Hours
M – S -10:00 – 5:00, Sun. – 11:00 – 3:00
DCA Member
Twigs & Teacups
Twigs & Teacups is a store dedicated to the art of gift giving. We have an eclectic assortment of items for any occasion! Our assortment of kitchenware, clothing, books, toys, and odds and ends ranges from old school to quirky, and from classic to modern.
410-778-1708
111 S. Cross Street
Chestertown
Days Open
All
Hours
Mon-Sat: 10-5, Sunday: 12-4
DCA Member
Walnut & Wool
Clothing.  Furniture.  Home Decor

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(410) 778-9000
321 High Street
Chestertown, MD 21620
Days Open
Sun, Mon, Wed, Thurs, Fri, Sat
Hours
Sunday & Monday Noon – 5 pm, Wednesday & Thursday Noon – 6 pm, Friday Noon – 7 pm, Saturday 10 am – 7 pm,
Bee Crafty Collectibles
Upcycled vintage furniture, home decor, custom wooden signs, gift shop
410 778 0479
Business Tags
335 High Street
Chestertown, MD 21620
DCA Member
Bohemia Trading Company
301 968 5778
7400 Church Hill Rd
Chestertown, MD 21620
Hours
Thurs/Fri/Sat 11 – 5, Sun 12 – 5
DCA Member
The Finishing Touch
Located in the heart of Chestertown, MD, we specialize in custom framing, fine art, select gifts, artist’s materials, digital imaging and art reproduction.
410 778 5292
311 High Street
Chestertown, MD 21620
Days Open
All
Hours
Mon – Thurs 9:30 – 5:30, Fri & Sat 9:30 – 7, Sun 11 – 3
DCA Member
Tiny Tots Boutique
Tiny Tots Boutique is a locally owned and operated clothing business that offers a large selection of well-made kids’ wear. Once you shop with us, you’ll keep coming for more. We carry fashion-forward clothes for boys and girls. All of our merchandise is high quality. You also don’t have to worry about high boutique prices, as we have priced our clothing products affordably.
443 282 0100
Business Tags
114 A S Cross Street
Chestertown, MD 21620
Days Open
Sun, Wed, Thurs, Fri, Sat
Hours
Wed 11 -3, Thurs 11 – 4, Fri 11 – 5, t 10 – 4, Sun noon – 3
DCA Member