Share on Facebook
Share on Twitter
E-mail this article
Leave a Comment
Print this Article

Its riverfront location makes Chestertown, Maryland, a picturesque getaway.

Situated on the west bank of the Chester River on Maryland’s Upper Eastern Shore, Chestertown is a blend of history, arts, shopping, and a variety of eclectic restaurants and accommodations. The Colonial town features a number of pre-Revolutionary War homes, a restored 19th-century general store, and an 18th-century tavern, along with a dozen or more galleries, studios, and shops featuring the work of local, regional, and internationally known artists and craftspeople.

Founded in 1706, Chestertown was soon named one of the Colony of Maryland’s six Royal Ports of Entry. A shipping boom followed and, considered Maryland’s second leading port, the town enjoyed much prosperity. The growing merchant class of the time built gracious brick mansions and townhomes, many of which still remain today; indeed, Chestertown is second only to Annapolis in its number of existing 18th century homes. Some of the finest examples are the large Georgian homes that line the Chester River along the south side of town, many built by wealthy shippers. Chestertown’s good fortune is owed to the fact that the city was mostly spared during the American Revolution.

Another point of Chestertown pride is Washington College, founded in 1782 (George Washington himself was a founding patron) and the 10th oldest college in the U.S.

Chestertown is a walker’s paradise, but if you’re more athletically inclined, rent a bike and take a ride through the rural landscape that surrounds the town or rent a kayak and take a paddle on the Chester River.

Then again, you can always just find the nearest bench down by the river and take in the view!

Fun fact

Washington College is known nationally as the home of the Sophie Kerr Prize, which is awarded to the graduating senior with the most literary potential. The award is nearly $50,000 annually.

Not to miss

Kent County Self-Guided Tours

Historic Chestertown and Kent Co. Tours (410-778-2829)

Yarmouth Tours (410-778-3221)

For those with an independent streak, a number of self-guided tours are available: Take a walking tour of Chestertown’s historic district or a self-guided audio tour of the Historic Chestertown Waterfront; follow the bike routes on Kent County’s flat and lightly travelled roads or tour the area by car on the meandering country roadways; or discover the beautiful shoreline of Kent County in your canoe or kayak or explore the Chesapeake Bay and its rivers on your boat. Guided walking tours are also available.

Schooner SULTANA


SULTANA is a reproduction of a Boston-built merchant vessel that served for four years as the smallest schooner ever in the British Royal Navy. Manned by a 25-person crew, the original SULTANA patrolled the coastline of colonial North America from 1768 to 1772, enforcing the hated Townsend Acts or “Tea Taxes.” From this vantage point SULTANA and her crew had a unique perspective on the conflict that would ultimately become the American Revolution. Departing and returning from SULTANA’s home port of historic Chestertown (and occasionally other ports around the Chesapeake), SULTANA’s two-hour public sails are a great way to sail the Chester River onboard a traditional schooner. Passengers are encouraged to help raise the sails, steer using Sultana’s seven-foot long tiller, and explore the authentically reproduced crew’s quarters below-decks.

Geddes-Piper House

101 Church Alley


The Historical Society of Kent County is housed in the historic Geddes-Piper House. The house contains an impressive collection of 18th and 19th century portraits, furniture, textiles, attire, maps, and china. The display of 18th and 19th century Chinese export tea pots is a major attraction. There is also a Victorian Children’s Room and changing exhibits which highlight local and Eastern Shore history.

Save the date

Through June 14

National Music Festival at Washington College


The Festival’s fourth season brings together world-class mentors and gifted apprentice musicians on the cusp of their professional careers. The two groups rehearse and perform together at Washington College and throughout Kent County in orchestral, chamber, solo recital, vocal, choral, and chamber opera repertoire. (Rehearsals are free and open to the public, and children are welcome.)

June 21

Grand Opening Charles Sumner Post#25, G.A.R.

10 a.m.–6 p.m.

206 S. Queen St.


Built by Black soldiers returning from the Civil War, this building was used as the meeting place for the Union Veterans organization, Grand Army of the Republic (G.A.R.). It has been restored and become a community center/museum/performance venue. This Juneteenth celebration features re-enactors of B Company, 54th Massachusetts Volunteer Infantry. The Festival will include not only Civil War encampment history re-enactments, but also music, games for children, tours of the building, and a fish fry and crab cakes (if you’re in Maryland, a crab cake can’t be far away!).

June 24

Literary House Series: Summer Poetry Salons

4:30 p.m.

The Rose O’Neill Literary House at Washington College


Stop by for an afternoon of poetry, local music, food and drink, and good conversation about the literary life.

Saturdays (until Christmas)

Downtown Chestertown

9 a.m.

For a selection of fresh produce and fine arts and craft by local artists, visit the weekly Chestertown Farmer’s Market and Artisan’s Market, located on Park Row in the heart of downtown Chestertown.

Bookmark it