Five Things to Do in Chestertown, Maryland

An pleasant destination for a day-trip or a weekend getaway

Historic Chestertown is located in Kent County on Maryland’s Eastern Shore. Founded in 1706, this town located at the head of the Chester River was named of Maryland’s six Royal Ports of Entry. Trailing Annapolis, it was considered Maryland’s second leading port. Today, Chestertown’s rich colonial history can be seen along High Street, the historic waterfront, and the replica Schooner Sultana. This fall, plan on making a trip to Chestertown, keeping some of our favorite autumn activities in mind.

Downrigging Weekend, October 26-28


Apart from the Chestertown Tea Party Festival in May, Sultana Education Foundation’s Downrigging Weekend is the most anticipated event of the year in this Eastern Shore town. The weekend features Chesapeake maritime experiences on and off the water, from tall ship sails, deck tours, lectures, and exhibits, to 5Ks, a half marathon, and other family activities. Each night of the festival, the tall ships will be illuminated along the docks; the docks at the Chestertown Marina close at dusk, but viewing is available along Chestertown’s waterfront. On Friday evening at 7 p.m., there will be a spectacular free fireworks display over the tall ships and the Chester River. Other highlights of the weekend include free public tours of the visiting tall ships, as well as the chance to actually sail on these vessels. Ticket prices vary by ship and sail times vary each day. Learn more and reserve your spot. Classic cars and boats will be on display at the foot of High Street, and there will also be a Dock Dogs competition, free, family-friendly concerts (including a performance by the Eastport Oyster Boys), and maritime-focused talks to round out the weekend. 

Sail on the Schooner Sultana

You don’t have to come for Downrigging Weekend to see the Schooner Sultana, a reproduction of the 1768 Boston-built merchant vessel that served for four years as the smallest schooner ever in the British Royal Navy. The community effort to build the replica schooner began in 1997 under the direction of Master Shipwright John Swain and scores of volunteers who aided more than 200,000 hours of labor. More than 10,000 people attended the launching of the Sultana in March of 2001. Since its launch, the Sultana Education Foundation has offered themed public sails on the Sultana, including an ecology sail, where guests help to pull a sampling net onboard to catch fish, crabs, and other critters from the Chester River; and a music sail where guests are entertained by local band Lions of Bluegrass. Ecology and Public Sails are $30 for adults and $15 for children under 12, while music sails are $35 for adults and $20 for children under 12. The final public sails will be October 26, 27, and 28. Learn more about each sail and purchase tickets here.

Take a History Tour

The Historical Society of Kent County offers a variety of history tours focusing on specific aspects of the town’s heritage. The museum is open Wednesday through Saturday from 10 a.m. to 3 p.m. with walking tours of Historic Chestertown available during regular museum hours for $15 per person (group tours must be scheduled in advance). If the paranormal interests you, the final evening of Ghost Walks will be held Saturday, October 27 beginning at 6:30 p.m. and running every half hour until 8:30 p.m. Chestertown boasts more 18th century homes in use than any other Maryland community except for Annapolis, and while not all are “haunted,” many have rather unique and often strange stories from their pasts. From the tales of a haunt in the attic of the house where George Washington really did sleep, to the Court House Ghost that made international news a few years ago, guides will walk ticket holders through centuries of stories, told against a backdrop of local history. Tickets are $12 for adults and $5 for children 12 and under. Tickets may be purchased by phone, online, or at the time of tour if available.

Attend a Festival

For a small town, there’s plenty going on throughout the year apart from Downrigging Weekend. The Chestertown Jazz Festival Weekend, held September 5-10, was an exciting colaboration between Rock Hall’s Mainstay Theater, Chestertown’s Garfield Center for the Arts, and other key local influencers. The annual town-wide Chestertown Harry Potter Festival October 5-6 was a blast for fans young and old alike. The festival benefits the arts in the local community and includes such events as a Quidditch tournament, scavenger hunt, charms class, Enchanted High Tea, a costume contest, wandmakers, an Azkaban prison break, and more. As we move into winter, the town will be transformed into Victorian-era London for a A Dickens of a Christmas, December 8-9. The event celebrates Charles Dickens and his famous novella, “A Christmas Carol,” with carriage rides, street theater, high tea, a holiday house tour, authentic food and drink, a “Run Like the Dickens 5K, and more themed activities. 

Visit Washington College

Washington College’s main campus is located on Washington Avenue, with its 18th century structures—the Custom House, Patrick Henry House, and Hynson-Riggold House—located near the foot of High Street on the Chester River. The college’s Boathouse is just downriver. The Washington College was founded in 1782 by William Smith. General George Washington gave the “College at Chester” a founding gift of 50 guineas, the largest made toward the founding of the college, agreed to serve on the Board, and gave permission to use his name. Washington served on the Board of Visitors and Governors for five years until 1789, when he became President of the United States. Click here for a schedule of upcoming tours and open houses.