Chestertown

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On the banks of the Chester River lies what seems to be a quiet, unassuming town. You wouldn't even notice Chestertown, Maryland unless you took another look. However, in the eighteenth century, Chestertown was the second largest shipping port in the state of Maryland. Today, it's second only to Annapolis in its concentration of historic eighteenth century homes. Some of the finest examples are the large Georgian homes that line the Chester River along the south side of town, many built by wealthy shippers. Chestertown's good fortune is owed to the fact that the city was mostly spared during the American Revolution.

Through the years, Chestertown's shipping industry dried up. However, other institutions have moved in to fill the void in the city's economy. Chestertown is home to Washington College, the tenth oldest liberal arts college to be chartered in the nation and the oldest college in Maryland. Chestertown also serves as the Kent County Seat. It's enough to keep this small town thriving so many years after its hey day.

Although Chestertown is a college town, the ambience in the city's downtown is more of a quiet village on the water than a hip urban center. The college's influence is only felt moderately on many of the town's businesses, which cater more to the day trippers then the local college crowd. For example, you'll find numerous antique stores and gift shops. However, one thing you would expect in a college town—book stores—are plentiful in Chestertown with no less than three offering new and used books.

Chestertown has two Main Streets that intersect with each other—High Street and Cross Street. The city is a must stop for anyone touring Maryland's upper Chesapeake region. The drive itself is very scenic and an attraction in itself.

Retail Hours

Although many shops and restaurants are open on Sundays, many are closed or have limited hours, so you may want to visit on a Saturday.

Parking

Chestertown has plenty of parking but many of its on-street parking is metered.

Restrooms and Visitor's Center

Public restrooms are located at the Kent County Visitor's Center located at the intersection of Church Hill Road (Maryland Route 213) and Cross Street. Since you'll most likely enter Chestertown on Church Hill Road, the Visitor's Center can be a convenient first stop when visiting the city.

Events

The Chestertown Tea Party Festival is held once a year in May. It's a chance to celebrate the city's famous act of rebellion during the Revolutionary War with events, entertainment, vendors, and even a reenactment of the Chestertown Tea Party. The original Chestertown Tea Party occurred when colonists dumped tea into the Chester River shortly after hearing news of Boston's own act of defiance in the face of having its port closed.

Tips

No visit to Chestertown would be complete without a stop at Stam Drugs (215 High St., 410-778-3030). Although it may seem like a typical mom and pop pharmacy from the outside, inside they feature an actual soda fountain just like your parents used to visit years ago. It's definitely worth it if you want to rest your feet while enjoying a cold refreshment.

A trip to Chestertown can be combined with a trip to Chesapeake City, about a half hour north.

Directions

Chestertown is about 75 miles from either Baltimore, Maryland or Washington, DC, and about 87 miles from Philadelphia, Pennsylvania.

From Baltimore, take I-97 south to U.S. 50 east/301 north. From Washington, take U.S. 50 east until it merges with U.S. 301 north. Continue on U.S. 50/301 across the Chesapeake Bay Bridge until the two routes split. Follow U.S. 301 north towards Wilmington. Take exit 25 for Maryland Route 213 north towards Centreville. Proceed for about 18 miles before crossing the Chester River. Turn left at North Cross Street (Maryland Route 289). The intersection of Cross and High is the center of town.

From Philadelphia, take I-95 south to Delaware exit 4A for Delaware Route 1 towards Christiana. Take exit 136 for Middletown Odessa Road (Delaware Route 299) and head right. Turn left at Middletown Warwick Road (U.S. 301) and travel about 17 miles. Turn right at McGinnes Road (Maryland Route 544) and travel for about 9 miles. Turn right at Church Hill Road (Maryland Route 213). You'll cross over the Chester River. Turn left at North Cross Street (Maryland Route 289). The intersection of Cross and High is the center of town.

External Links

www.chestertown.com

Directory

Antiques

AH Kepner Design Studio (201 High Street, 410-778-3415)
Antiques on Cannon (306 Canon Street, 410-778-1138)
Chestertown Antique Mall (200 High Street, 410-778-9006)

Apparel

Empty Hangers (114 South Cross Street, 410-778-1300)
Houston's Dockside Emporium (315 High Street, 410-778-9079)
Nearly New Shop (320 High Street, 410-778-1781)

Arts and Crafts

Artworks (306 Park Row, 410-778-6300)

Books

Bookplate (112 South Cross Street, 410-778-4167)
Chestertown Old Book Company (113 South Cross Street, 410-810-3880)
The Compleat Bookseller (301 High Street, 410-778-1480)
Feed the Soul Bookstore (314 Park Row, 410-778-2214)

Children's

Pride and Joy (321 High Street, 410-778-2233)

Coffee and Dessert

Dunkin Donuts (315 High Street, 410-778-6211)
Play It Again Sam's (108 South Cross Street, 410-778-2688)
Stam Drugs (215 High Street, 410-778-3030)

Dining

Blue Heron Cafe (236 Cannon Street, 410-778-0188)
Brix Tapas Kitchen & Wine Cellar (337 High Street, 410-810-2749)
Crossfire Cafe (117 South Cross Street, 410-778-0871)
Feast of Reason (203 High Street, 410-778-3828)
Fish Whistle (98 Cannon Street, 410-778-3566)
The Imperial Hotel (208 High Street, 800-295-0014)
New York Kosher Style Deli (323 High Street, 866-579-3140)

Florists

Dutch Blooms (312 Park Row, 410-778-0912)

Footwear

Paul's Shoe Store (227 High Street, 410-778-2860)
Scottie's Shoes and Consignments (307 High Street, 410-778-4944)

Framing

The Finishing Touch (311 High Street, 410-778-5292)

Galleries

The Artists' Gallery (239 High Street, 410-778-2425)
Artworks (306 Park Row, 410-778-6300)
Carla Massoni Gallery (203 High Street, 410-778-7330)
The Finishing Touch (311 High Street, 410-778-5292)

Gift Shops

Artworks (306 Park Row, 410-778-6300)
Cornucopia of Treasures (110 Cross Street, 410-810-2952)
Houston's Dockside Emporium (315 High Street, 410-778-9079)
Kerns Collection (210 High Street, 410-778-4044)
Twigs and Teacups (111 South Cross Street, 410-778-1708)
Village House (103 South Cross Street, 410-778-5766)
Wood Carvings Etc. (308 Park Row, 410-810-7999)

Home Furnishings

AH Kepner Design Studio (201 High Street, 410-778-3415)
David Ferguson Oriental Rugs (241 High Street, 410-810-0603)
Empty Hangers (114 South Cross Street, 410-778-1300)
Lauren Ames Interiors (114 South Cross Street, 443-282-0558)
Nearly New Shop (320 High Street, 410-778-1781)
Robert Ortiz Studios (207-C South Cross Street, 410-810-1400)

Jewelry

Boyer's Jewelers (106 South Cross Street, 410-778-1966)

Markets

Chestertown Natural Foods (303 Cannon Street, 410-778-6537)

Pharmacies

Chestertown Pharmacy (329 High Street, 410-778-2575)
Stam Drugs (215 High Street, 410-778-3030)

Sporting Goods

Bikework Bicycle Shop (208 South Cross Street, 410-778-6940)

Thrift Shops

Nearly New Shop (320 High Street, 410-778-1781)

Wine

Play It Again Sam's (108 South Cross Street, 410-778-2688)