Chestertown Charms

Shopping doesn't get more scenic or pleasant than drifting from store to store in this historic Eastern Shore town.

Focus On Shopping

April 25, 2004|By Elizabeth Large | Elizabeth Large,Sun Staff

The important thing to know about shopping in Chestertown on the Eastern Shore is that everything is two blocks away from everything else. That's only a slight exaggeration; the truth is you can park your car and happily spend the rest of the day on foot. What's more, the most interesting stores are located in the historic district. On a fine spring day, this Eastern Shore town is an easy, scenic place to shop.

Don't expect any chain stores. Rumor had it that a Chico's was going to move in, but that never materialized. Instead, Chestertown offers a mix of traditional small-town stores and intriguing, more upscale shops. Surprisingly, tourists seem to enjoy the former as much as the latter. They appreciate the personal service.

There's nary a Starbucks in sight, but Chestertown does have several nice little cafes where you can get lunch or afternoon tea. Hours of both shops and restaurants vary widely; this time of year you'll find more places open toward the end of the week.

The stores, antique shops and galleries are too numerous to list them all here, but the following will give you some idea of the more unusual ones. If you stop at the Kent County visitor center (Cross Street and Rt. 213) on your way into town, you'll find maps, a complete listing of stores and galleries, and public bathrooms. Leave your car in the parking lot there and walk the two blocks to High Street, where many of the shops are located. Or look for the three other free lots. You can also park on High; bring quarters for the meter.

Carla Massoni Gallery

203 High St.


Leave your expectations at the door. This is like a New York gallery on the Chesapeake Bay, filled with contemporary art both abstract and traditional. "My absolute commitment was there would never be a duck in here," says owner Carla Massoni. She represents fully established artists with national and international reputations such as sculptor Bart Walter and painter Greg Mort.

* Not-so-guilty pleasure: If you're a beginning collector, you can find beautiful pieces for under $1,000.

Twigs & Teacups

111 S. Cross St.


Everyone mentions this pretty little shop when you ask about shopping in Chestertown. Here are things useful and not-so-useful, tchotchkes and inexpensive oddities. You can find kitchenware and wrapping paper, seasonal items and toys. All of it is presided over by Hobbes, a very large cat.

* Not-so-guilty pleasure: An array of wonderful little dipping sauce dishes, many Asian inspired, both individual and sets for $3 up.

Chester River Knitting Co.

306 Cannon St.

410-778-0374, 800-881-0045

Each sweater is knit on hand-operated machines with all-natural yarns, and you can watch. Custom design your own, or choose from the many in stock. The Chester River Knitting Company also carries ladies' ready-wear from other craftspeople and boutique manufacturers. Sweater prices run from $75 up to $500 for cashmere.

* Not-so-guilty pleasure: A hemmed raglan sweater jacket for $145, the company's version of the classic Chanel jacket.

Kerns Collection

210 High St.


Think of this store as a miniature version of the ACC crafts show. The owner, Susan Kerns, is an artist and an interior designer. She buys intriguing handmade things and displays them beautifully, mostly clothing, jewelry and home accessories. Upstairs are lamps and a little bit of furniture.

* Not-so-guilty pleasure: Beautiful framed prints, some signed, and very affordable.

Ship's Store at the Sultana Center

107 S. Cross St.


The Sultana is a 1768 reproduction schooner, a project undertaken by a nonprofit educational organization based in Chestertown. This small shop is filled with toys, books, gifts, clothes, artwork and home accessories related to the ship.

* Not-so-guilty pleasure: Lots of different sailing ship models for under $100.

Cornucopia of Treasures

110 S. Cross St.


This is a gift store extraordinaire, with a bridal registry, home and garden accessories, and an extensive baby and children's section. Its handmade jewelry, good-quality silk flowers, stationery and Crabtree & Evelyn products are big sellers. It also offers some items that aren't so easy to find, like Vietri & Casafina glassware and upscale Caldrea household cleaners.

* Not-so-guilty pleasure: Pretty little wind chimes with the word dance or dream and butterflies, hearts and beads for $13.95.

Ehrman Tapestry

112 S. Cross St.

410-810-3032, 888-826-8600

Marylanders knew this as an Ellicott City-based mail-order company for upscale needlepoint kits. When owner Marjorie Adams moved to Chestertown, she opened a chic little retail stop as well. The stock includes embroidery and needlepoint kits from England, knitting yarns, the Kaffe Fassett line of linens, and decorative items for the home.

* Not-so-guilty pleasure: Readymade needlepoint shoes with floral and dog designs for $125.

J.R.'s Antiques

114 S. Cross St.


This isn't one of those dusty little shops crammed with old things, but room after room of well-displayed antiques and collectibles from the 18th century to the 20th. Much of the merchandise is from estate sales and people who want to downsize, so there's lots of furniture, Oriental rugs, china, accessories and sterling flatware. As the sign says, no bartering.

* Not-so-guilty pleasure: A fine selection of Chinese export porcelain at reasonable prices.


Chez Barbe

315 High St.


Casual but imaginative lunches like crepes and crab cakes.

Feast of Reason

203 High St.


The simple menu of lunches like quiche or spinach salad changes daily.

Kettledrum Tea Room

117 S. Cross St.


Elegant English teas but also lunch and dinner.

Old Mill Bakery & Cafe

207 S. Cross St.


Sandwiches, salads and entrees like shepherd's pie and quesadillas.

Play It Again Sam

108 S. Cross St.


A coffeehouse, wine bar and lunch spot rolled into one.

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