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 one of Maryland’s six Royal Ports of Entry and the 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; styles become more modern closer to the main square, starting with 300-year old Georgian Colonials at the waterfront and modernizing to 100-year old Victorian 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.” Even so, the business district has plenty of parking lots scattered about to make it convenient for those who want to drive from place-to-place.

Historic District

Chestertown Visitor Center
Chestertown Visitor Center

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.

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

Lawyer's Row in Chestertown, Maryland
Lawyer’s Row

Continue down 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 younger, built in 1860.

An interesting aside — behind the courthouse is Lawyer’s Row (100 Church Street), unbelievably small buildings housing 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.

Geddes-Piper House, home of the Kent County Historical Society
Geddes-Piper House, home of the Kent County Historical Society

Around the corner of Lawyer’s Row on Church Alley is the Geddes-Piper House (101 Church Alley), Kent County HIstorical Society headquarters. It was a merchant’s home built in 1783 and is still set up as if colonials still lived there. The original kitchen is still in the basement. This is the best chance to see the inside of one of Chestertown’s Georgian homes

You can catch afternoon tea there and a walking tour of historic Chestertown. The historic house is open for a self-guided walk through on the weekends for a small donation. Check the website for the times because they change depending on the season.  And make it an earlier stop as they may lock-up before closing time if things are slow.

Click here for a guide to Chestertown’s historic buildings.



Downtown/Business District

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.

Saturdays 8am - Noon
Chestertown Farmers Market

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.

On one side of the park is Park Row with a number of artisan shops: a wood carver, weaver, printer, sewing shop and upholsterer. 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. It was once a bustling retail area, but now has several empty stores. But take note of the Dunkin Donuts, or rather, what’s behind the chain store in the middle of the block. 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

There are a number of specialty shops on the side streets that are worth visiting. Walk behind the High Street stores and you’ll come across Cannon Street, with a natural foods store, knitting company and Treasures Re-Found with “collectibles & useful items.” It’s an antique store, but one that’s full of unusual stuff and simply fun to walk through.

Row of Chestertown Artisan Shops
Row of Chestertown Artisan Shops

Across the street is a yellow house, which is actually a row of artisan shops. A sign in front advertises Sparky’s fresh brown eggs, “laid by happy chickens wandering around the yard.”

The first gallery is The Tree of Light American Craft Gallery run by two sisters. Faith Wilson makes painted canvas floor coverings that have shown in the Smithsonian, as well as DC & Baltimore galleries. Marilee Schumann is a potter who shows throughout the East Coast.

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.

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.


To the 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.

White Swan Tavern
White Swan Tavern

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.

Garfield Center for the Arts & Imperial Hotel
Garfield Center for the Arts (left) & Imperial Hotel (right)

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.


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.

Chestertown Customs House
Chestertown Customs House

The Custom House (101 S. Water Street) is open for free tours Fridays 12pm 4pm & Saturdays 11am 4pm. That’s where you can get a free audio tour of the House and of the immediate neighborhood. 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.

Inside the Customs House
Inside the 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 that could have been used a jail. A tour of the basement is available upon request.

Water Street Houses Circa 1740
Water Street Houses Circa 1740

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.)

In that park is the Washington College pavilion with covered bench seating made for watching the riverDSCN1656 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. 

Chestertown Boardwalk
Chestertown Boardwalk
Colonial homes from the Chestertown waterfront boardwalk
Colonial homes from the Chestertown waterfront boardwalk

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.

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
Widehall, built in 1769, is listed on the National Register of Historic Places
Widehall, built in 1769, is listed on the National Register of Historic Places

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.

This area is a National Historic Landmark district with some of Maryland’s best examples of 18th and early-19th century houses, according to the federal government. The report mentions River House (107 N. Water Street) and Widehall (101 N. Water Street), both are private and not open to the public.


Washington College

Washington College Quad
Washington College Quad

Up the hill, about a mile from the historic area, is Washington College (300 Washington Avenue) founded in 1782 with General George Washington contributing 50 guineas and his name for the cause. He served on the board until becoming U.S. President. It was the first college chartered in the colonies, and the tenth oldest college in the United States.

It’s a busy, attractive campus with a quad ringed by some historic buildings, but it’s not particularly worth a tour if you’re in Chestertown for just a day-trip.




Seasonal Activities

Each Saturday morning, from April through Christmas, the town hosts a farmer’s and artisan market in the town square, Fountain Park. It’s one of the biggest on the Eastern Shore with locally grown seasonal produce, along with local soaps and other homemade products. The bakery items are killer.

The town hosts a number of festivals during the year, best known for Downrigging Weekend in the Fall, featuring the Schooner Sultana. It’s one of the largest “tall ship” and wooden boat festivals on the East Coast, started in 2001 to mark the end of the sailing season for the schooner Sultana. The Sultana is a remake of the Royal Navy schooner HMS Sultana.

In the Spring, it’s the Chestertown Tea Party Festival commemorating the local merchant’s revolt against the British tea tax in 1775, five months after the more famous Boston Tea Party.

Merchants there still do things the Chestertown-way.  For example, two-dollar bills and one-dollar coins aren’t collectors items there; merchants distribute them regularly as change with the philosophy that  it’s common sense to reduce coins in the pocket and bills in the purse. That’s just how Chestertown rolls.