Places to stay in Chestertown, Maryland

Photos: Miles River Guest House, Elk Forge Bed and Breakfast Inn, Retreat & Day Spa

Click to reserve Chestertown hotels online with Stay Maryland

The Brampton Inn

Inns / B&Bs: Finished in 1860 as the plantation house of the area's largest peach grower, Brampton retains today nearly all of its original details, including the magnificent three and a half story walnut, ash and heart pine central staircase, walnut windows and doors, original heart pine floors, and plaster .....

25227 Chestertown Road, 21620, (+001) 410-778-1860

Click property titles for more detailed descriptions

Chestertown links of interest

• Other Maryland locations ..
• Chestertown Chamber of Commerce

Nearby towns close to Chestertown, Maryland

Situated on a scenic peninsula where the Chester and Sassafras rivers meander into the Bay, Kent County has retained its serene beauty despite the passage of time. Our enchanting coastline varies from historic waterfront towns dotted with marinas of all sizes to stretches of low, rolling farmlands broken only by the tidewater tributaries of the Chesapeake. This land, where fresh and salt water meet, is a veritable haven for fishing and boating enthusiasts, cyclists, birders and nature lovers. It is also an immense refuge for a variety of plant and animal life, and we make every attempt to protect them, sometimes to the chagrin of seasonal hunters.

Visitors eager to explore the tidal shore can discover numerous aquatic birds including ducks, geese, kingfishers, heron, osprey, bald eagles and other water-loving creatures who make their homes along the reeds and rushes. These estuarine habitats offer nearly ideal spawning and nursery conditions for many fish species, including alewife, shad, blue fish, perch, oysters and the blue crab. Striped bass, known locally as "rockfish" is perhaps the most prized fish found in these surrounding waters.


Locals think of Kent County as "quintessentially rural," and the community displays a grace and fluidity almost unknown in today's hurried marketplace. Farming and agriculture constitute a large portion of the economy, and during the summer months local markets brim with fresh produce at bargain prices.

Located on the banks of the Chester River, Chestertown dates back to 1706 when it served as a thriving mid-Atlantic port of entry for the colonial movement into Maryland. Along with being a prosperous shipbuilding and trading center, Chestertown became a locus for government and court. In fact the County's court records are the oldest in the State, dating back to the 1640s.

The Chester River curls past grand homes of wealthy merchants from the 18th and 19th centuries. Among the town's finest historic buildings are the Hynson-Ringgold House, renowned for its unusual antler staircase and hip roof, and Wide Hall, a masterpiece of Georgian architecture built in 1769 by Thomas Smyth, Kent County's most prosperous merchant and an illustrious Revolutionary War figure. An old Customs House dating from the 1740s stands beside the public dock at the foot of High Street. Its detailed Flemish Bond brickwork is commonplace in many old town residences.

Welcome visitors can follow quaint red-brick sidewalks along broad shaded streets as they roam through specialty shops, galleries, antique stores and eateries on their way to one of several exquisitely restored B&Bs in town. On fine summer weekends, evening concerts are often held around the antique fountain in the town square. The secret splendors of Chestertown, however, are the beautiful walled gardens tucked behind the alongside historic homes.

History comes to life through the annual Chestertown Tea Party, reenacted each Memorial Day weekend. This festival celebrates events of May 23, 1774 when, on the heels of the news that the Port of Boston had been closed by the British, local residents boarded the Brigantine Geddes, which had dropped anchor in the Chester, and angrily consigned its shipment of tea to the depths of the River.

A must on every sightseer's itinerary is Washington College, the tenth oldest liberal arts college in the country. It was founded in 1782 with the help of George Washington, who gave his name and 50 guineas in appreciation of Kent County's supplying flour to his troops, as well as the patriotic acts of our citizens during the War.

As George Washington, Thomas Jefferson and James Madison traveled from Virginia to Pennsylvania, they came ashore in picturesque Rock Hall (eight known times for George to be exact) on the Annapolis Ferry, then journeyed by horse north to Philadelphia to hammer out American Independence.

• Kingstown - 0 km
• Worton* - 4 km
• Church Hill - 6 km
• Kennedyville - 7 km
• Crumpton - 8 km
• Still Pond - 8 km
• Price - 9 km
• Rock Hall* - 10 km
• Betterton - 10 km
• Grasonville* - 18 km
• Queenstown* - 15 km
• Galena* - 13 km
• Centreville* - 11 km
• Edgewood* - 19 km
• Earleville* - 16 km

Towns are shown withing 20km radius of Chestertown, Maryland. Distances are not representive of traveling amounts. Towns marked * indicated accommodations listed.