Things to Do in Chestertown, Maryland

Sultana is a full-size reproduction of a 1768 schooner, built in Chestertown by thousands of students and volunteers and launched in 2001. Public sails last two hours on the Chester River. You can help raise the sails, take a turn at the seven-foot tiller and poke around the crew’s quarters below deck.

★ Good to know Sails leave from the Chestertown Marina at 207 S. Water St.; children under 5 can’t board.

The Historical Society of Kent County’s self-guided tour has 29 stops. They range from grand colonial houses to vernacular homes and key sites of African American history. It was first produced in 1985 and expanded in 2024. Brochures are available outside the Bordley History Center at 301 High St. seven days a week.

★ Good to know The society also runs guided group tours and ghost walks by reservation, booked at least two weeks ahead.

In May 1774, townspeople passed resolves against buying, selling or drinking tea. Local legend says they then threw a ship’s tea into the Chester River. The free festival over Memorial Day weekend reenacts the ‘tea toss’ from the Sultana. There are parades, historical walking tours, raft races, colonial music and crafts.

★ Good to know A parade down High Street to the river opens the festival.

Each year from late October into early November, Chestertown’s waterfront fills with visiting tall ships. Kent County calls it one of North America’s largest tall ship festivals, with sailing trips, music, author talks and local food and drink.

★ Good to know Dates shift each year; check the Sultana Education Foundation before you plan.

Founded in 1782, Washington College is the tenth-oldest college in the country, and George Washington was a founding patron. Its Middle, East and West Halls are on the National Register. The college also awards the Sophie Kerr Prize, worth about $50,000, to the graduating senior with the most literary promise.

★ Good to know The college hosts public lectures, and Main Street Chestertown’s bike share has a depot on campus.

Every Saturday morning, year-round, farmers, bakers and artisans set up along the 200 and 300 blocks of High Street around Fountain Park. Expect produce, meats, cheeses, breads, flowers and handmade goods.

★ Good to know It runs 8 a.m. to noon, so come early for the best selection.

Main Street Chestertown counts more than 200 shops, galleries, restaurants and bars in and around the brick-lined downtown. On the first Friday of each month, shops and galleries stay open into the evening. The Kent County Visitors Center can point you to the best cream of crab soup in town.

★ Good to know Bike share bikes are parked at the marina and Washington College; you unlock them with the Movatic app.