Chestertown is in Maryland's Eastern Shore. Chestertown, the county seat of Kent, the Eastern Shore of Marylands's oldest county, was founded in 1706 and served as a port of entry during colonial times. A town rich in history, its attractions include a blend of past and present. Its brick sidewalks and attractive antique stores, restaurants and inns beckon visitors and residents alike to wander through the historic district and enjoy homes and places with architecture ranging from the Georgian mansions of wealthy colonial merchants to the elaborate style of the Victorian era. Chestertown is situated on a scenic peninsula where the Chester and Sassafras rivers meander into Chesapeake Bay.
The best way to get around Downtown Chestertown is on foot. Everything you need to see is within walking distance and it's nice to stroll the brick sidewalks to see the sights. The main shopping area is on High Street and Cross Street, and the beautiful historic houses lining the water are just two blocks from the main strip of boutiques and restaurants.
The college is a very short drive away from the downtown area. Once there, it is easy to walk around the pretty campus and take the same steps that George Washington once did over 300 years ago.
The Chestertown Farmers Market is located in Fountain Park on Park Row in the heart of downtown Chestertown at 118N Cross Street. It is open every Saturday morning from the first Saturday in April until the last Saturday before Christmas. The market includes a variety of produce as well as meats, cheeses, soaps and lotions, and baked goods.
Washington College is located in Chestertown. Washington College is a private liberal arts college that has roughly 51% in state students and 49% out of state students. The college was founded in 1782 and is the tenth oldest college in the United States.
The Chester River can be easily accessed by going all the way down High Street, passing the Imperial Hotel on the left.
The first Friday of each month, many stores in the downtown area pariticpate in what is known as "First Friday". Participating stores and gallerys extend their hours for gallery viewing and shopping.
Rachel's Flower Power is a small, upscale boutique located at 210 High Street, directly next to the Imperial Hotel. The store is quickly becoming known as one of the most popular and unique stores in Chestertown. The shop has fresh and unique flowers that are not found anywhere else in Chestertown. The store does flower arrangements on the spot as well as deliveries and a large amount of flower arrangements for weddings and all types of events. In addition to the special hard-to-find anywhere else flowers, the shop sells many gifts and is well known for its gift baskets. It is very popular with the locals and tourists, as it is a great place to pick up a souvenir. The website to Rachel's Flower Power: http://www.rachelsflowerpower.com/
Antiques on Cannon is located at 306 Cannon Street. The store collects antiques as well as unique recycled items. http://www.antiquesoncannon.com/index.htm
The Front Room at the Imperial Hotel is one of the most popular and high-end restaurants in town. Many locals and tourists find it to have the best food in Chestertown. There is an extensive wine list and the menu is filled with a variety of different choices, using fresh, regional ingredients. The restaurant offers seating outside during the Spring, Summer, and Fall seasons in the courtyard.
Play it Again Sam's (108 South Cross St) is the towns only coffee shop offering fresh brewed coffee, tea, pastries and some hand selected wine for sale by the bottle. You're likely to be in line next to some Washington College students and professors or the regulars around town. Many out of towners consider this a near perfect coffee shop!
Andys is a lounge-style bar. Individuals must be 21 years or older to enter. It is a non-smoking restaurant and bar that offers music as well as weekly specials such as "tapas Tuesday" and "meatloaf Monday". The food menu and drink menu change seasonally.