Chestertown Antique and Furniture Center 6612 Church Hill Road, Route 213, Kingstown, MD 21620, 410-778-5777, Chestertown Antique and Furniture Center always features a new inventory of high quality antiques, reproductions and used furniture and collectibles. It is open Monday through Friday from 10 a.m. to 5:30 p.m. more... 

J.R.'s Antiques and Collectables 114 South Cross Street, Chestertown, MD 21620, 410-810-1006, An antique shop offering a fine selection of furniture, antiques, rugs, glassware and other collectables. The shop inventory is always changing and you never know what you might find. more...

Ehrman Tapestry 112 Cross Street, Chestertown, MD 21620, 410-810-3032, Located in the heart of historic Chestertown. Needlepoint art kits, needles, floor stands, and more. more... 

Chesterton Old Book Company 113 Soouth Cross Street, Chestertown, MD 21620, 410-810-3880, This store specializes in providing rare and secondhand books. Here you can find books from the 17th Century to the present. They offer fine bindings, sets and other unique items as well as locating out of print books. more... 

Compleat Bookseller 301 High Street, Chestertown, MD 21620, 410-778-1480, This outstanding independent bookstore offers a large selection of classic and contemporary reading material for the whole family. Book signings, lectures and special events are held on a regular basis. You'll also find a nice selection of gifts for all ages here. more... 

Houston's Dockside Emporium 315 High Street, Chestertown, MD 21620, 410-778-9079, Apparel shop offering quality gifts and clothing for men and women with a regional flavor including Woolrich, Sportif, Sigrid Olsen, Royal Robbins, David Brooks, Ingenuity, The New Englander Rain Jacket Shell, scarves, ties, belts, handbags, hats, and ladies jewelry. more...

Pride & Joy Incorporated 321 High Street, Chestertown, MD 21620, 410-778-2233, Unique children's apparel, great Christening outfits and gifts. Gift registry for expectant mothers is available in the store. more... 

Sweater Makers 306 Cannon Street, Chestertown, MD 21620, 410-778-0374, Exquisite line of handmade sweaters and knitwear from natural fibers. Some items available are tanks and vests, cardigans, crews, tutlenecks, and v-necks.  more... 

Kerns Collection, LTD 210 High Street, Chestertown, MD 21260, 410-778-4044, An exquisite collection of fine art, crafts, and jewerlry. Open Monday thru Thrusday, 10a.m.-5p.m., Friday and Saturday, 10a.m.-5:30p.m. more... 

Finishing Touch 311 High Street, Chestertown, MD 21620, 410-778-5292, 800-292-0457, A large picture frame shop offering custom framing, decorator frames, local prints; as well as, art supplies, greeting cards, and other general gift items. more...

Cat's Paw 21144 Green Lane, Rock Hall, MD 21661, 410-778-1342, The Cat's Paw is a unique clothing and gift shop at the Sailing Emporium Marina. Items available include clothing for men, women and children, books, stationery, jewelry, toys, Chesapeake memorabilia, and cat themed items. more...

Cornucopia of Treasures 110 Cross Street, Chestertown, MD 21620, 410-810-2952, Located in historic downtown Chestertown, Cornucopia has a large selection of unique items including Crabtree and Evelyn, stationary and greeting cards, handcrafted jewelry, Vietri and Casafina glassware, music, baby and children's items, fountains, garden items, and a large selection of silk flowers.

Ditty Bag 20880 Rock Hall Avenue, Rock Hall, MD 21661, 410-778-6697, Located in the Haven Harbor Marina, this gift shop offers everything from bikinis and shoes to books and pant suits. more...

Marian Fry 9818 Augustine Herman Highway, Chestertown, MD 21620, 410-778-1539, A collection of fine jewelry including diamonds, gemstones, and sterling silver. 

Sweet Annie's 5753 North Main Street, Rock Hall, MD 21661, 410-639-7991, Located in the Shoppes of Oyster Court, this unique boutique offers decorative hand soaps, candles, beaded jewelry, potpourris, herbal pillows, essential oils, and many other fine gift items.

Twigs & Teacups 111 South Cross Street, Chestertown, MD 21620, 410-778-1708, A unique collection of ceramics, glasswear, windchimes, linens, lotions, stationery, books, and toys. more...

Durding's Store 5742 North Main Street, Rock Hall, MD 21661, Located at the Corner of Main and Sharp Streets, 410-778-7957, Enjoy real fountain drinks and homemade ice cream at Durding's, an authentic old-fashioned candy store with an original marble fountain and stainless soda fountain. You will also find greeting cards and gifts. more...

Sweet Rick's Candy and Fudge Shop 5797 Main Street, Rock Hall, MD 21661, 410-639-7700, Sweet Rick's specializes in chocolates that are hand made, hand molded, or hand dipped. They even make their own fudge with real butter and cream. Sweet Rick's also offers real soft serve ice cream, fresh baked cookies, shaved ice, Via Veneto Italian Ice, and the unique candy trains. more...

David Ferguson Oriental Rugs 241 High Street, Chestertown, MD 21620, 410-810-0603, Offers customers one of the finest selections of old and antique Oriental rugs from Persia, Turkey and the Caucasus to be found anywhere. more...

Chesapeake Seaglass PO Box 156, Chestertown, MD 21620, 410-778-4999, Hand made creations designed by Chestertown, Maryland artist Nancy LaMotte using genuine pieces of seaglass. Created items for sale include bracelets, necklaces, pendants, pins and earrings in up to 14 different colors. more...

Smilin' Jake's Casual Apparel 5774 Main Street, Rock Hall, MD 21661, 410-639-7280, Smilin' Jake's is a store full of island fashions and t-shirts. more...

Rock Hall Liquors 21318 Rock Hall Avenue, Rock Hall, MD 21661, 410-639-2177, A liquor warehouse with "the coldest beer in town," Rock Hall Liquors offers a large selection of wine, liquor, and ales along with Maryland lottery tickets, cigars and cigarettes, snacks, party supplies, and ice.