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1

Bloomin Wild

335A High Street Chestertown, Maryland 21620

A full service florist offering fresh cut flowers and specialty arrangements for all occasions. Our selection includes blooming plants, herbs, succulents and vegetable plants. Gift include soap and chocolate from artisans, garden decorationsÔÇô

410-778-5300
2

Bookplate

112 South Cross Street Chestertown, Maryland 21620

Used books, local and regional history, signed first editions, imported mediteranean ceramics and tiles.

410-778-4167
3

Bordley Center

301 High Street Chestertown, Maryland 21620

Extension of the Kent County Historical Society.

410-778-1111
4

Boyer's Jewelers

106 South Cross Street Chestertown, Maryland 21620

Fine Jewelry

410-778-1966
5

Charles Sumner Post #25

206 South Queen Street Chestertown, Maryland 21620

The historic building will become a world-class museum with an exhibition about the nation's Civil War and the story of African Americans' involvement in it.

410-778-1149
6

Chester River Wine & Cheese Co.

117 South Cross Street Chestertown, Maryland 21620

Chester River Wine & Cheese Co. is a retail store specializing in wine, cheese, olives, cured meats, pate, and other gourmet specialty provisions. We also offer wine by the glass, cheese and charcuterie boards for onsite consumption.

443-282-0220
7

Chestertown Farmers' Market

High Street Chestertown, Maryland 21620

One of the most popular features of a weekend visit to Chestertown is a stop at the Farmers' Market. You'll find bread, fresh home-grown produce, plants, herbs, and even -occasionally- puppies and goats. Don't miss it!

410-639-7217
8

Chestertown Natural Foods

303 Cannon Street Chestertown, Maryland 21620

Natural and organic foods and products, produce, vitamins, gifts.

410-778-1677
9

Chestertown RiverArts Gallery

Suite 106 315 High Street Chestertown, Maryland 21620

Non-profit community arts center offering gallery exhibits, weekend craft & art workshops, and a gift shop featuring the work of Eastern Shore artists and artisans.

410-778-6300
10

Chestertown Used Book Store

6612 Church Hill Road Chestertown, Maryland 21620

Primarily hardbacks, non-fiction and fiction, most areas of interest, mostly from Estates, 95% are $5 or less

410-778-5777
11

Doug Ashley Realtors

227 A High Street Chestertown, Maryland 21620

We will provide you with comprehensive and quality service, from helping you search for your new home, assist you in negotiating, to making sure that everything is signed sealed and delivered on settlement day.

410-810-0010
12

Empty Hangers

114 South Cross Street Chestertown, Maryland 21620

Clothing from your favorite designers from traditional to contemporary, chic to funky and classic to modern. We also carry household items and children's ware.

410-778-1300
13

Eve's Cheese

302 Park Row Chestertown, Maryland 21620

Six varieties of cheese processed using milk from Fawnwood farm in Kent County.

410-778-5968
14

Gabriel's of Chestertown

207 South Cross Street Chestertown, Maryland 21620

Trendy, Classic and Coastal gift shop and boutique. Enjoy a unique selection of clothes, accessories, home & party goods, and children's items.

410-778-2123
15

Garfield Center for the Arts

210 High Street Chestertown, Maryland 21620

The Garfield Center is a multi-function community center for the performing arts offering theater, music, film and children's programming throughout the year.

410-810-2060
16

Hegland Glass

315 High Street Chestertown, Maryland 21620

Contemporary kiln-formed art glass.

410-870-5432
17

Houck's Menswear

200 High Street Chestertown, Maryland 21620

Our purpose is to provide high quality American made products to the Eastern Shore of Maryland and beyond for young men and older gentlemen.

443-282-0026
18

Houston's Dockside Emporium

315 High Street Chestertown, Maryland 21620

Traditional to trendy clothing for women and men, accessories, sterling silver and costume jewelry, gifts, books. Exclusive Chestertown dealer for Chesapeake Bay Throws. Crab knives.

410-778-9079
19

Kent County Arts Council

115 Philosophers Terrace Chestertown, Maryland 21620

Kent County Arts Council helps fund, support, and produce the arts in our community. KCAC supports community events, school cultural arts presentations, and individual artists.

410-778-1149
20

Lauren Ames Interiors

203 High Street Chestertown, Maryland 21620

Home furnishings, antiques & interior design

443-282-0058
21

Massoni Art

203 High Street Chestertown, Maryland 21620

Contemporary fine art: paintings, sculpture, photography, and prints. We will be limiting our exhibitions and eliminating standard gallery hours. Private appointments may be scheduled.

410-778-7330
22

Mimi's Closet

307 High Street Chestertown, Maryland 21620

Our always changing inventory features elegant women's clothing from Nina Mclemore and new, exciting designers like Lesley Evers, Boo Gemes, Before & Again tees, Anni Kuan and much more.

443-282-0225
23

Music Life

241 High Street Chestertown, Maryland 21620

Music Life and The Eastern Shore School of Music provide an environment where students of all ages and skill levels can experience the pleasure of making music. Lessons-Instruments-Sales-Repairs

410-778-7010
24

Occasions Catering / The Boardroom

327 Cannon Street Chestertown, Maryland 21620

Custom catering for memorable events. Also available is a private location for meetings and conferences in downtown Chestertown.

410-778-5122
25

Play it Again Sam

108 South Cross Street Chestertown, Maryland 21620

Located in the heart of downtown Chestertown, Play It Again Sam serves a complete line of coffee offerings, breakfast and lunch specialties, snacks and wine.

410-778-2688
26

Robert Ortiz Studios

207 South Cross Street Chestertown, Maryland 21620

Handmade in Chestertown, contemporary furniture in the Shaker and Japanese Traditions

410-810-1400
27

Skippy's Riverside Gifts & More

227 High Street Chestertown, Maryland 21620

Our gift shop has handmade gifts from many local artists that make a wide range of products. We also do custom orders on Gourds, Bottles, and other items. Also here at Skippy's we do Signs, Sublimation Printing, Awards, TrophiesÔÇô

410-778-2073
28

The Artists' Gallery

239 High Street Chestertown, Maryland 21620

Fine art by featured local artists: paintings, photography, pottery, superior woodcraft and more.

410-778-2425
29

The Collection

112 South Cross Street Chestertown, Maryland 21620

An eclectic blend of fine art, antiques and modernism. Services include art appraisals, restoration and hand washing and repair of Oriental rugs.

443-282-0040
30

The Creative Focus

400 South Cross Street Chestertown, Maryland 21620

Portrait photography studio; specializes in newborns, children, families and graduating seniors

410-810-1411
31

The Finishing Touch

311 High Street Chestertown, Maryland 21620

Select gifts, fine framing, artist's materials, digital imaging

410-778-5292
32

The Nearly New Shop

320 High Street Chestertown, Maryland 21620

Clothing and household items. All sales benefit Chester River Hospital Center Auxiliary.

410-778-1781
33

The Stam Drug Company

215 High Street Chestertown, Maryland 21620

Full service pharmacy, old fashioned soda fountain & ice cream, and gifts.

410-778-3030
34

The Sultana Center

107 South Cross Street Chestertown, Maryland 21620

Sultana Projects Educational Center

410-810-3009
35

Treasures - Refound

315 High Street Chestertown, Maryland 21620

A wide variety of antique furniture, clocks, glassware, costume & estate jewelry, cast iron, art glass, yard art, art (paintings and prints), decoys and many more unique antiques and collectibles.

410-708-7989
36

Tree of Life Gallery of American Craft

312 Cannon Street Chestertown, Maryland 21620

Marilee Schumann and her sister Faith Wilson, are operating a decorative arts gallery in Chestertown, Md.

410-708-4652
37

Twigs and Teacups

111 South Cross Street Chestertown, Maryland 21620

Gifts, toys, cards, soaps, linens, apparel, amusements useful and useless.

410-778-1708
38

Village House

103 South Cross Street Chestertown, Maryland 21620

Celebrating 25 years of classic design, we offer an array of carefully selected home furnishings. Unique lamps, silk lampshades, needlepoint pillows, luxurious throws and other finishing touches.

410-778-5766
39

Washington College Bookstore

300 Washington Avenue Chestertown, Maryland 21620

Textbooks, current reading materials, apparel and school supplies.

410-778-2800
40

Woodcarvings, Etc.

308 Park Row Chestertown, Maryland 21620

Hand-carved, one-of-a-kind woodcarvings and collectibles.

410-810-7999