The Geddes-Piper House of Chestertown, MD, is a tall narrow townhouse of weathered brick and crisp white trim with a hefty wooden door. The house has stood on this spot since 1783, its condition waxing and waning as much of Chestertown grew up around it.

But in a town full of lovely historic buildings, the Geddes-Piper House isn’t remarkable for its age, its restoration, or the people who have called it home. It’s remarkable for its contents.

The Geddes-Piper House is now the home of the Kent County Historical Society and a member of the Chesapeake Bay Gateways Network. Here, the stories of its people and landscape are collected and retold, helping local families appreciate their roots and introducing visitors to the heritage of this scenic peninsula on the Bay’s upper Eastern Shore.

Executive Director Karen Emerson said the society’s goal is to offer a “gateway” to the Kent County experience, just as Kent County is a gateway to experiencing the Chesapeake Bay.

“Our goal is to prepare people to go into the county and have the whole experience, to encounter the farms and the towns and the watermen, and see how a lot has stayed the same, even after hundreds of years have gone by,” Emerson said.

Kent County is one of Maryland’s oldest defined colonial places. It was officially founded in 1642. At the time, it included Kent Island, east of modern-day Annapolis, from which the county drew its name.

The earliest colonial settlements along the Chesapeake thrived on tobacco crops, and Kent County was among them. Life revolved around plantations, held by men who often took title to blocks of land in hundreds and even thousands of acres, making towns unnecessary.

Labor from enslaved Africans and indentured servants delivered profit for plantation owners, but Kent County in the 1600s was a still a rough-hewn place. Roads were few. Water was the primary link to other settlers and the world beyond.

In 1706, the British government imposed some order on the situation. The act for the “Advancement of Trade and the Erection of Ports and Towns” created Chestertown on the banks of the Chester River and made the town an official control point for the import and export of goods.

Social life and material wealth were set to blossom.

“Chestertown became one of six royal ports in Maryland, and it was a major one, at one point bigger than Annapolis,” Emerson said.

By the 1730s, planter families in Kent County were thriving, along with maritime trade and the merchants who dealt with the wide array of goods that moved through the harbor at the end of High Street.

Tobacco gave way to grain as the major export, departing for the West Indies, Spain, the Azores and Madeira on ships that returned with fruit, wine and salt.

“Anything coming in and out had to go through the customs house, so people had easy access to all kinds of luxuries, like citrus fruit for their fancy punches. Everything you could want was here,” Emerson said.

Chestertown also became an important stop on the north-south land route through the colonies.

Travelers heading to Philadelphia would cross the Bay on a ferry between Annapolis and Rock Hall, then pass through Chestertown on their way to Delaware. George Washington came to town several times, as did Thomas Jefferson, Patrick Henry and James Madison.

The land where the Geddes-Piper House now stands entered the public record in 1730, when port activity was booming.

Bricklayer James Moore was its first owner, later followed by customs inspector William Geddes, who bought the property in 1771.

To visit today, take a tight turn near the main avenue into a short, narrow street called Church Alley that’s packed tight with old buildings. In Geddes’ time, though, it was a largely cleared lot just one street from the working waterfront.

“It was a bustling place,” Emerson said.

Geddes sold the property to James Piper in 1784. Piper was a prosperous merchant, and he likely built the Geddes-Piper house that stands today. But the fervor of Chestertown’s maritime trade began to fade after the Revolutionary War, and this may be reflected in Piper’s choices — he subdivided and sold about two-thirds of the lot, then moved to Baltimore about 10 years later.

By the 1830s, the Wescott family owned the house and kept it for nearly 100 years. The Wescotts built an addition on the rear of the home that reflected their status.

“They were wealthier, part of the upper middle class, so they wanted to put the kitchen on the main level and have a large formal dining room,” Emerson said.

The historical society replaced the floor of the addition after they bought the house in the 1950s, but the planks used were salvaged from the county’s old almshouse barn and date to the 1830s or earlier. Most of the woodwork in the rest of the house is original.

The rooms of the first and second floor, as well as the basement kitchen and hallways, are brimming with snippets of Kent County life from the 1600s to the mid-1900s.

The displays don’t highlight the rich and famous, although they give an understated nod to a bed and fire screen from James Alfred Pearce, who served in the U.S. Senate in the years before the Civil War, and to the local roots of the classic 20th-century movie actress Katherine Hepburn.

Most pieces provide a sense of the personal and, in some cases, the ordinary — from dressing gowns for infants and a set of slender satin slippers to period furniture, toys and pieces of smoking pipes found on site.

“What’s my favorite thing about the house? Everything,” Emerson said.

In the front parlor, sitting unobtrusively by the hearth, is a small cannonball that was found at Caulk’s Field. Not far from town, Caulk’s Field was the site of a battle during the War of 1812 where American militia turned back British soldiers who were burning local farms.

Hanging by a nearby window, on paper so thin it seems to shimmer, is an original British land grant that dates to 1732.

A second floor bedroom includes framed samplers on age-stained cloth. Seven-year old Sarah created hers in 1845, while 12-year old Faithy Trumball stitched wavy lines in1893. A collection of quilt squares are signed with the names of local women hailing from places like Buck Neck, Great Oaks Manor and Fancy Farm.

There’s plenty of memorabilia from the Tolchester Beach amusement park, which opened in 1877, and a tea set from the popular Bay steamer, the Emma Giles.

Even a Ouija board makes an appearance. Many people credit Chestertown cabinetmaker Ernest Reiche with inventing it.

Emerson is amused by the way some stories overlap.

One involves a fireplace mantle. John Piper, the home’s builder, had a business partnership with a man named Frisbee. The original front parlor mantle was relocated to the Frisbee house in the early 1900s. “A total coincidence, because the homes were owned by completely different families by then,” Emerson said.

A large, lovely china collection came from Woodland Hall, where part of the Wescott family lived. The Wescotts who owned the Geddes-Piper House likely ate from these same dishes when they visited.

Family ties were convoluted. “Everybody was related to everybody else,” Emerson said.

The Geddes-Piper House is now one of the best places to untangle those ties. The third floor contains the research library, which includes family records, ledger books from local businesses, newspaper clippings, oral histories, maps and photographs.

“People come from all over the world to do research here,” Emerson said. “Recently, we’ve had researchers from Canada and Africa, and we have members all over the United States. One member in Hawaii has never been here, but he’s got family history in Kent County, so he supports us.”

In the hallway, an old map depicts a bird’s-eye view of Chestertown in 1907.

In the map, Chestertown is roughly shaped like the letter T. The short edge is at the waterfront, dense and thick. The base of the T extends inland, longer but narrow and tenuous in comparison. It’s the visual story of a community moving inland, but one that won’t let go of its watery roots anytime soon.

Geddes-Piper House

The house museum is open year-round 10 a.m. to 4 p.m. Tuesdays through Fridays. From May through October, the house is also open 1–4 p.m. Saturdays. It is closed on Mondays.

The historical society library is open 10 a.m. to 3 p.m. Wednesdays through Fridays.

Admission to the house museum and library is free.

  • History Happy Hours take place 4–6 p.m. the first Friday of most months and include wine, cheese programs, and discussion. The event is free but a donation from non-members is appreciated.
    Group tours and teas are available but must be scheduled in advance. They include (fee is per person):
  • Tours of the Geddes-Piper House. Fee: $3.
  • Walking Tour of Historic Chestertown. Fee: $15.
  • Afternoon Tea. Fee: $15.
  • Afternoon Tea & Walking Tour. Fee: $25.
  • Chinese Export Tea Pot Program. Fee: $5.

For information, visit or call 410-778-3499.

The Geddes-Piper House is a short walk from the homeport of the schooner Sultana. The Sultana, a member of the Chesapeake Bay Gateways Network, is a replica of a British ship that patrolled the North American Coast just prior to the American Revolution. For a port schedule and event information, visit or call 410-778-5954.101.

For information about other sites in the Chesapeake Bay Gateways and Watertrails Network, visit