Chestertown – History, Art and a Party Spirit

Chestertown is one of the most historic and quaint colonial towns on the upper Chesapeake Bay. Located on the beautiful Chester River, on the Eastern Shore, the town was Maryland’s primary port for the upper Eastern Shore.

That meant local crops left out of Chestertown for Europe and the Caribbean. In exchange, ships brought European goods to the colonies. The waterfront is lined with large historic homes once owned by wealthy merchants. Only Annapolis has more 18th century homes in Maryland.

Walking away from the water is like going through a architectural time warp, starting with 300-year old Georgian Colonials at the waterfront, moving through Victorian, and gradually modernizing to 150-year old Gothic homes.

Chestertown is small, at just over 5,000 residents. The entire historic area is walkable. As one resident put it, “I can walk to everything I need except a grocery store.”

The streets are lined with large shade trees encircled by river-rock or slate, making both attractive and comfortable summer walking.

If walking isn’t your thing, Chestertown has plenty of parking lots scattered about to make it convenient for those who want to drive from place-to-place.

Chestertown’s Historic District

Chestertown Customs House (corner), now a museum

Chestertown’s entire downtown and waterfront are in the historic district. If you drive in, you’re likely to come in on Cross Street and you’ll go by the Kent County Courthouse (103 N. Cross Street) and Emmanuel Episcopal Church (101 N. Cross Street). They share the same square.

“There has been an Episcopal Church at the corner of Cross and High Streets since about 1706,” according to the church website. The current church has been there only since 1767. The courthouse is slightly newer, built in 1860.

An interesting aside — behind the courthouse is Lawyer’s Row (100 Church Street), unbelievably small buildings that house lawyers’ offices. Some look just big enough to fit a desk, some files and a bit of seating area. They’re still in use as offices.

Chestertown’s Downtown

The main business section surrounds Fountain Park. Yes, there’s a fountain there, topped with the goddess of Youth and Beauty. The big, green Victorian fountain hasn’t maintained its youth or beauty but the town is proud of it. The iron fountain was renovated in 2008.

Chestertown, MD, town square
Fountain Park in Chestertown

Chestertown is well known for its Saturday morning Farmers’ & Artisans Market in Fountain Park. It’s big. Only home-grown produce and home-made products are allowed to be sold there. The baked goods are amazing. The artisans are vetted by the association that runs the market. Saturdays 8am-noon, April through Christmas, although some venders may show up through the winter in good weather.

Chestertown Farmers Market

On one side of the park is Park Row with a number of artisan shops. You won’t notice just driving through, but Chestertown is loaded with artisans. More on that in a bit.

Shops are found along High Street. Boutiques are mixed in with a distillery and restaurants. Take note of the hidden areas, such as an art studio behind the Dunkin Donuts. A walkway leads to modern art studios and River Arts (315 High Street), a community arts gallery and gift shop.

Items there can range from a $10,000 wood sculpture to a $50 hand-woven wool scarf. River Arts has a list of the artisans scattered throughout town. These are artists who regularly show their works in juried shows from New York to DC.

Across Cross Street from Fountain Park is Monument Park, a little park with war monuments providing a shady place to relax.

Next to it are some interesting buildings, including: Stam’s Hall, a Beaux Art pharmacy & store on the first floor and meeting/banquet rooms for rent on the second floor. The bell tower still rings on the hour.

Off the Beaten Path Downtown

Circle around and walk down Cross Street towards downtown and you’ll come across a number of unique gift shops, including a used-book store and a coffee house.

Walk behind the High Street shops and you’ll come across Cannon Street with more artist studios.

Row of Chestertown Artisan Shops

Many of the artisans are often away from their studios on the weekends at art shows. However, Chestertown RiverArts convinces them to stay in town and open their studios to visitors two weekends a year, allowing visitors to “buy original work at studio prices.” River Arts has the schedule and a map with the location of the studios.

On the Way to Chestertown’s Waterfront

High Street is the main road that takes you to the waterfront, or from the boat to downtown, and it’s a pleasant walk gradually changing from turn-of-the-century commercial to colonial residential.

You’ll stroll past the White Swan Tavern (231 High Street), a restored colonial inn. It’s not a public tavern. It’s now a B&B that offers an afternoon tea; you must make reservations to participate in the tea. They also serve lemonade or coffee and pastries.

White Swan Tavern
White Swan Tavern

The Imperial Hotel, (208 High Street) has been a Chestertown meeting place for over a century. Built in 1903, it’s been renovated and is still in use as a hotel/restaurant, offering 50-cent oysters during happy hour Tuesday-Wednesday (4pm-6pm) when in season.

Next door is the Garfield Center for Arts (210 High Street), a restored art deco theater with performances and art films.  Both are worth a walk-through.

Several shops are in that area, along with the Evergrain Bread Company (201 High Street), a laid-back kind of place specializing in crusty artisan breads, pastries, coffee. Their sandwich selection is limited, but highly unique. They rival the rural baked goods found at the Saturday Farmers Market. There are outside tables, and the establishment encourages folks to hang out for a while.

Chestertown’s Waterfront

Colonial customs house in Chestertown, MD
The Custom House in Chestertown

The waterfront is where it all began. The street paralleling the Chester River is Water Street. And that’s where the big colonial merchant houses are. Many are privately owned. Some are owned by Washington College and used for special events.

The Custom House (101 S. Water Street) is the only one regularly open for tours (Fridays & Saturdays). 

It was built in 1746, the home of Thomas Ringgold, said to be one most active slave traders in this Chesapeake Bay region. Later, it became a warehouse and a store and eventually turned into a customs house.

The upper half of the Custom House is restored and rebuilt to it’s original colonial-ness.

The basement houses an archeological dig lab where the kitchen once was. It still has open hearth fireplaces and a root-cellar with iron bars. The backstory on those bars is evolving. Only a few years ago, tour guides said it was likely a customs jail. Now, it’s historians think it might have been a holding pen for slaves.

A tour of the basement is available upon request.

You can get a free audio tour of the Custom House and the immediate neighborhood at the Custom House. You give them  a valid drivers license, and you get an i-Pod shuffle containing a series of public radio-style stories on the history and people who started Chestertown.

Water Street is worth a walk from end to end. If you’re facing the river, a right will take you past a couple salt-box houses to a park. (There’s parking there if you drive to the riverfront.)

Water Street Houses Circa 1740

In that park is the Washington College pavilion with covered bench seating made for watching the river flow by, or more likely, rowing and sailboat races. It’s a great view of the Chester River and there are several benches facing the river along a short walkway.

On the way back toward High Street, you’ll go by the Chestertown Marina (211 S. Water Street) with the Fish Whistle restaurant (98 Cannon Street) where you can get a table on the porch overlooking the water. They feature bands on Friday and Saturday nights, making it a lively place on the weekends.

If you come by boat and are docked at the marina, the main square is only a couple blocks away up High Street. 

But continue to the other side of the marina and there’s a boardwalk across a bit of marsh. It’s a great view of the colonial houses from the waterside and of the river.

Near that boardwalk is the slip where the Schooner Sultana is docked during season. It’s a full size replica of a Boston merchant ship that served in the British Royal Navy for four years. She’s a wood boat with tall wood masts and huge canvas sails. An impressive sight under sail. You can catch a ride on weekends. Check the website for times and prices.

Schooner Sultana (photo courtesy Sultana Education Foundation)

If you walk down the boardwalk, you should return by walking the rest of Water Street to see the other post-Revolutionary, Federal-style homes.

Flemish bond wall, notice the enamel-covered smaller bricks
Flemish bond wall, notice the enamel-covered smaller bricks

Many of these Chestertown houses were built using Flemish bond brick on the street side and American bond on the sides. Basically, Flemish bond is a more stylish and expensive way to lay brick walls.

If you drive in, the Visitors Center (400 High Street) at the corner of Route 213 & Cross Street is a good first stop. It has parking near the main square, bathrooms and a friendly person to answer questions. They’ll let you know if anything interesting is going on that day.

The visitors center has a well done self-guided walking tour brochure/map of historic Chestertown.

Chestertown Visitor Center

About Those Chestertown Parties…

Chestertown has some of most popular festivals around the Chesapeake Bay.

Downrigging Weekend | Photo Courtesy Sultana Education Foundation


Taste of Chestertown

Early May – Restaurants from Kent County’s finest dining establishments set up in Fountain Park for samplings of their signature dishes. From classic Maryland dishes like crab soup to nouvelle gourmet dishes. Sampler plates cost 1-3 tickets. Beer and wine available by the glass

Chestertown Tea Party Festival

Memorial Day Weekend – One of the best festivals on the Eastern Shore. In May of 1774, Chestertown forbid importing, selling, or consuming tea in town in response to the British closing the Port of Boston. According to local legend, residents then gathered at the town center, marched down High Street to the waterfront and tossed a cargo of tea overboard. The annual reenactment of that event is the centerpiece of the Chestertown Tea Party Festival. Party goers are encouraged to dress in colonial costume.


Kent County Fair

Mid July — You’re chance to attend an old-fashioned county fair. This 4H fair features a horse show, dog agility contest, a petting zoo, rides, and plenty of vendors. The greased pig contest and the 4-H livestock and cake auctions are popular fair events. 

Pirates & Wenches Weekend

Mid August – Pirates Weekend is actually in nearby Rock Hall, but it’s a short drive and a big event on the Chesapeake Bay. Hundreds of normal people dress as pirates for the weekend long, town-wide party every August. There’s pirate-themed events for kids and different ones for adults, lots of pirate music and vendors from across the region.


Chestertown Jazz Festival

Early September – Thursday, Friday & Saturday of jazz found in venues throughout town.

Harry Potter Festival

October – Grab your wand, hop on your broom, and come for a weekend of magic at the annual Chestertown Harry Potter Festival. Explore the colonial river town and join in on the spectacular activities and events, for children and adults—wizards and witches alike. >>CANCELLED FOR 2021<<

Sultana Downrigging Weekend

End of October – This is the last hurrah for Chesapeake Bay historic Tall Ships. Many of the larger towns have wood schooners, war ships or sloops that local groups maintain and travel throughout the Bay during the summer as traveling history lessons.

Hosted at the end of the schooner SULTANA’s sailing season (late October or early November), Downrigging attracts thousands of visitors to Chestertown to sail on the assembled fleet of ships, listen to great music, and support the Sultana Education Foundation’s education programs.


Holiday High Tea & Christmas Readings at Brampton Inn

December – Colonial re-enactor Stokes Tomlin dresses in historical period garb and reads holiday-inspired literature such as Truman Capote’s “A Christmas Story.” Guests gather in the parlor, they light the fire, and the fun begins! The readings normally last about 30 minutes. Then, everyone gathers in the dining room, we pour some wine, and some delicious food is served.

Oyster Festivals

Oyster season starts in the Fall and ends in the Spring. Bars, restaurants and lodges (aka American Legion, Elks, etc.) host oyster fests throughout the winter. This is where you go to get good, inexpensive oysters.

Chestertown Map

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One thought on “Chestertown – History, Art and a Party Spirit

  • June 9, 2021 at 12:52 pm

    My aunt was Leone Woodall. I spent a lot of time with her and a lot of time
    In Chestertown until her death. I love Chestertown, it has always been my favorite of all places and miss it very much. It was my happiest place.

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