Places to stay in 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 on the Annapolis Ferry, then journeyed by horse north to Philadelphia to hammer out American Independence. Local dining options include Play It Again Sam, Luisas Cafe, Ellen's Coffee Shop, and China House.

If you are travelling in the area, Chestertown is located close to Chestertown Business Park, Bookers Hollow, Kennedyville Volunteer Fire Company Station 4, Grays Inn Creek and Mount Pleasant Church.

Available Chestertown lodging

We currently have 18 accommodations in and around Chestertown.

Chestertown Hotels, Motels, Resorts, B&Bs and Extended Stay

Chestertown Camping & RV, Cottages, Rentals and Lodges / Ranches

Other useful links:

• Chestertown Chamber of Commerce
• Chestertown, Maryland on Wikipedia

Things to see and do, places to eat in Chestertown

Fish Whistle ( Dining / Seafood ). Located at 98 Cannon Street. At Fish Whistle it's all about the food and the stunning scenery! There are plenty of fresh fish and seafood options to enjoy at our pet-friendly restaurant. Fish Whistle at the Granary gives you beautiful views of the Sassafras River. Sit on our outdoor deck and enjoy nice summer breezes and when the chill comes back in the air, come inside and sit by one of our warm fireplaces. You will enjoy a wide variety of delicious food selections a full service bar and live entertainment on the lower deck every weekend during the summer. We look forward to serving you! fishandwhistle.com

Luisas Cafe ( Dining / Italian ). Located at 14 Washington Square. Our dishes are prepared with locally grown fresh ingredients from St. Brigid’s, K&B Market, Cedar Run, White Pines Produce, Red Acres Hydroponics and Redman Farms. Seafood, vegetables, poultry or meats… you’ll find them to be superb! www.luisasrestaurant.com

Renamed properties

• Red Roof Inn & Suites at 160 Scheeler Road may have been previously known as Quality Suites or Comfort Suites
• Comfort Inn at 150 Scheeler Road may have been previously known as Holiday Inn