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Today, Port Street is a somewhat forgotten part of town that many in Easton have lamented for years. In one archived Star Democrat letter published around the mid-20th Century, a resident recalled the once-booming port and its heyday.

“In one brief period … it was the clearing house of local trade, the focal point through which the passengers and freight to and from a growing town and community passed,� the letter reads. “Then came the railroads, the ferries, the motor cars and buses and trucks.� 

But property owners and town officials want to restore the street to its former glory and connect its newfound businesses and homes to the rest of Easton in one of the largest and most important projects the town has ever tackled.

Documentation of the street shows the area has a long history that will need to be taken into account as parties look to redevelop it — especially if the area is to be preserved or the history highlighted in the redevelopment plans. 

Easton Point, at the head of the Tred Avon river where the Tanyard Branch stream and Papermill Branch streams met, was once known as Cow Landing, Cowe Landing, Booker Point and Town Point, according to the 2008 book “925 Port Street,� a history of Port Street by local historian Priscilla Morris.

The point was used as a harbor by Native Americans long before European settlers came to Maryland in the 1600s. The first known white landowner was Samuel Tilghman, a goods trader and ship commander who bought 1,000 acres of property, including Easton Point, in 1659 and dubbed the land “Tilghman’s Fortune.�

Tilghman sold the property in 1664 to Francis Armstrong, a wealthy landowner with over 6,000 acres of property in Maryland at the time. Around 1711, Port Street was first connected to the town, which by then was mostly just the Talbot County Courthouse, a jail and a few small homes.

But Port Street’s connection to the town was “essential to the success of the court location during the 18th Century and for the rapid development of the town after the revolution,� Morris wrote.

Over the following decades, multiple landowners would buy up and own several different areas of Port Street, but the most notable was a Quaker family with the last name of Booker. The Bookers would end up owning most of Easton Point for 127 years.

In 1791, James Booker, a carpenter, saw Easton Point as a “gateway� for the town, Morris wrote. He sold multiple land parcels off to others who he felt would support the area as the “key to growth� in Easton, according to Morris.

Also around this time, a man by the name of Cloudsberry Kirby built 925 Port Street, which began as an inn but is now a historic home, one of the oldest in Easton. The county’s question as to the exact origin of 925 Port Street prompted Morris to write her book on not only the house, but the entire street.

Lambert Hopkins bought out Booker’s remaining property in 1797. Hopkins, a farmer and shoemaker, also sold and leased property to other landowners and spearheaded the development of the Port Street area and harbor.

In the 19th century, Easton Point was “the busiest passenger port on the Eastern Shore.�

Shipbuilder James Stoakes, along with captain and commander Clement Vickars, led this era of Easton Point, building ships and steamboats — including the famous steamboat Maryland — and overseeing a port bringing in goods that were vital for the whole town.

Easton Point was also a central port and trading center during the War of 1812. Vickars fought during the war himself aboard The Messenger, a ship built by Stoakes.

In 1820, 119 residents lived at Easton Point. Workers helped with the operations of the port and its many boats, including storage, freight and shipping. Important trade items include lumber, grain and coal.

Port Street was quickly becoming not only the largest place of business in Easton, but one of the most booming ports in Maryland, along with the harbors in Baltimore and Annapolis.

Other businesses at Easton Point in the 19th century included an oyster packing house, a steam sawmill and a peach packing factory.

At the turn of the century, Easton Point was still vital to the town but degrading in use after the invention of both railroads and automobiles. It had become a pleasure port around the 1930s, a welcome stop for yachts and sailors and even a stop for a traveling company, The Adams Floating Theatre, which hosted plays on a barge.

Still, Port Street would wane in the coming years. By the late 1950s and early 1960s, articles in the Star Democrat reflected a community’s growing concern with the deterioration of Easton Point, the “community’s gateway to the water.�

“It is being largely abused and ignored,� reads one Oct. 7, 1960, editorial in the newspaper, finding fault with abandoned boats and the county’s dumping of slag in the harbor. “Whatever the approach, care and development must replace abandonment and abuse. This, after all, is Easton’s waterfront ‘front yard.’ It should, as such, be made to create a good first impression for visitors. Nothing could do more to discourage visitors than one look at the county property as it stands now.�

At least one man was committed to restoring the area: Charles Ewing. He bought the marina at Easton Point and remodeled it for 23 boat slips. He created walkways and a car service for travelers coming in by boat.

But the county had largely ignored pleas to restore the street and harbor that was part of public property. Residents soon cried out for the government to at least dredge the area — removing silt and sediment buildup to clear the waterways — which it agreed to do in 1963.

By the 1980s, the largest operator at Easton Point was Arundel Corp., which still distributes oil from Port Street. Besides Arundel Corp., businesses at the point today include the marina, gas stations, a seafood restaurant and the material shipping company Vulcan.

By the late 1980s, some residents, including the Talbot Historical Society, had grown tired of the big oil and gas companies on the street, the neglected wharf and the abandonment of the old heart of town.

In 1988, the historical society voiced public disapproval of the county’s management of Easton Point, writing in a letter to the Talbot County Council that it had been neglected, despite holding much promise for the town.

“There remains of the shoreline of the North Fork of the Tred Avon, enough so that a small park could have been created between the shore and the parkway and Port Street,� the letter reads.

Nothing was done then, but the idea for a waterfront park caught on.

In August 1995, Easton held a public hearing on the annexation of more land from the county to the town. Then, the town of Easton owned about 15 acres of land near the point and operated a public works facility there, which still exists today.

Easton has held onto the idea of creating a public park. In 2020, the town made a huge advancement when it announced the purchase of property owned by oil and gas distributor Southern States.

On that parcel of land, the town proposes a waterfront park, including a boat ramp, green space and an amphitheater.

Other property owners plan to fulfill the long-awaited restoration of the harbor, announcing large-scale re-development — housing, restaurants, breweries and boathouses.

The history behind Easton Point is one narrative that many have warned should not be ignored as owners redevelop. It was neglected once, and could be neglected again if not done correctly.

Also, the history of the street should be memorialized and placed somewhere for visitors to see, some property owners have argued, including Easton Point 24 Fueling owner Tim Miller and John Schroeder, who runs The Boathouse.

“I wanted to turn it into a museum of historic nature,� said Schroeder. “The history of maritime on the Chesapeake Bay. Easton would not be here if it wasn’t for that river.�

Schroeder said he’s worried the direction the town is headed in — mostly large-scale housing — will mean the loss of Port Street’s history.

Miller said he would like to see a “riverwalk� stretching around Easton Point so tourists and residents can see the water and the historic harbor.

“There’s so much history down here,� he said, echoing the desire for “memorializing or preserving it somehow.�

One landowner on Port Street who has not commented on preservation is Paul Prager, who owns at least half of Port Street already and is planning to purchase more land.

Prager's vision includes building thousands of square feet of commercial space and at least 500 homes in the area.

Neither Prager nor Bluepoint Construction, his company in charge of the project, responded specifically when asked about preserving the history of the street.

Mayor Robert Willey said in an interview that history would not be lost as the town redevelops the aging port.

“I’m very familiar with the history down there and with what is going on,� Willey said. “There’s a very real desire to keep it that way, to fix it up and make it a destination.�

Willey said he was also hoping to reach an agreement to purchase the historic home of 925 Port Street, currently owned by the county, so it could be incorporated into the town’s design plans for Easton Point.

Talbot County currently has no plans for the renovation of the house or for the sale of it, according to the county.

The Easton Economic Development Corporation, a nonprofit established in 2013 and a major planner for Port Street’s renovation, has also hoped to preserve the area and its three homes: the Pratt-Hoffman House (925 Port Street), the William C. Knight House and a large home on the property of the retirement community Londonderry.

In the EEDC’s small area master plan, a rough blueprint for redeveloping the area, the organization suggested redeveloping the area with its history in mind. The best way to do that, the EEDC said, is to create recreational experiences and put people on the water.

“There would be an opportunity to provide a dynamic interpretive destination that would highlight the site’s importance to American history,� according to the master plan. “Ongoing revitalization projects can incorporate the history and values of this community into healthy community development initiatives based on the principles of respect for traditional roots, inclusivity, and active listening.�

A museum site could be one way to showcase and tell the story of the street, according to the master plan. A public park with panels could be another.

Tracy Ward, the executive director of the EEDC, agreed that Port Street redevelopment needs be tackled correctly and in a mindful way of both the past and present, calling it “a project that will be here long after everyone is gone.�

“We want it to last,� she said.