Once known as Head of Elk, named by Captain John Smith, Elkton sits at the northern headwaters of Chesapeake Bay. Its fortuitous location placed the settlement squarely on the principle north-south roadway in Colonial America. Its strategic advantages caused Head of Elk to be chosen by the British as the starting point for their attack of Philadelphia during the American Revolution. On August 27, 1777, three hundred ships carrying over 15,000 soldiers appeared in the Elk River. The British landed unopposed, stayed awhile in Head of Elk and marched to the nation’s capital which they occupied after pitched battles at Brandywine and Germantown. Four years later, the Marquis de Lafayette embarked his troops here in his pursuit of traitor Benedict Arnold. He was followed by George Washington who was marching his forces overland to ultimate victory at Yorktown, Virginia.

Elkton preceded Baltimore in the development of the flour-packing industry and was hailed by 1807 as an important wheat market, with trade having attained a level of 250,000 bushels per year. After the War of 1812, packet lines continued to run between Elkton and Baltimore, and the New Castle and Frenchtown Railroad that began in 1832 further increased Elkton’s importance as a transportation center. Numerous mills were established on the Elk River, evidenced by still-surviving millraces, and the town thrived. Prosperity waned for several decades in the financially precarious times of the 1830s but the post Civil-War years brought new industries, including pulp mills, machine shops, fertilizer plants and canneries to the town, stimulating housing construction in the late 1800s. It was Elkton’s Golden Age.

Elkton achieved national notoriety in the the 1920s and 1930s when northern states began to pass more restrictive marriage laws. Maryland did not and a number of border towns became known as places to get married quickly and without many restrictions, or “Gretna Greens.” Elkton, being the northeastern most county seat in Maryland - and thus closer to Philadelphia, New York, and New England - was particularly popular. It was “the elopement capital of the East Coast” and thousands of marriages were performed there each year. Some of the celebrities who got married in Elkton included actresses Joan Fontaine and Debbie Reynolds, singer Martha Raye, political figures John and Martha Mitchell, baseball great Willie Mays, and televangelist Pat Robertson. Even after the quickie-marriage was eliminated when the state passed a 48-hour waiting period in 1938, Elkton continued to be a place to marry, and especially elope. 

Our walking tour will start in the historic center of the old Head of Elk, only a few steps away from a marrying chapel...

Elkton Chamber & Alliance Visitor Center
101 East Main Street, northeast corner of North Street 

In 1783 this land was owned by Robert Alexander, a Tory, and was confiscated by the State. Trustees held the land for the erection of a Court House, Market House, and other public buildings. After the front portion of the building was demolished, the Town of Elkton purchased the property for use as Town Hall. Today the building fronts a small visitor center. 


Old Singerly Fire Hall
108 North Street

Organized in 1892, Singerly Fire Company is a volunteer organization serving the citizens of Cecil County, Maryland and the surrounding area. This building was the company’s first home. The ground floor was arranged for fire apparatus; the second floor served as Elkton’s municipal offices. A bell tower was constructed for sounding the fire alarm. At the time, the equipment consisted of an Amoskeag Steam Fire Engine, a fully equipped hook and ladder truck and two hose carts. Today, Singerly Fire Company responds to over 4,000 fire, rescue, and EMS calls every year - the most active fire company in Cecil County.

107 North Street

This building was constructed in 1915 to serve as a Ford dealership for Warren Boulden, who knew Henry Ford personally. Hitching rings were built into the wall. It was used as Boulden Ford until 1985. In 1988, the town of Elkton purchased and renovated the building.

International Order of Odd Fellows Hall
114-118 North Street 

This building was constructed as a lodge for the International Order of Odd Fellows in 1867. As a bustling center of social activity in Elkton, Walt Whitman lectured here in 1886 and some of the first motion pictures in Maryland screened in the auditorium on the second floor.

Mercantile County Bank
127 North Street

The Mercantile County Bank formed on January 1, 1908 and this Neoclassical home,  fronted by a pair of Ionic columns, shortly followed. PNC Bank purchased its assets in 2006.

Old Cecil County Jail
214 North Street

In July 1870 land was purchased from James Groome on North Street for the construction of a new jail. It replaced the first prison built in Elkton, also on North Street in 1791, where prisoners were literally chained to the floor. This new jailhouse featured 20 cells. A whipping post was set up and Cecil County’s first lashings since Colonial days took place beginning in 1896 here, inflicted with a cat-o-nine-tails. Hangings also occurred in the jail yard, the last one in 1905. The prison was abandoned after 113 years in 1984 when a modern detention center opened on Landing Lane at the edge of town.    

Bull’s Head Tavern
310 North Street

This small clapboard building stands on the site f the Bull’s Head Tavern that was the first stopping-off point from the Pennsylvania Railroad when it ran into Elkton a few feet away. There may be a few remnants of the early hostel lurking in the current building although it in no way approximates the structure of the Bull’s Head Tavern.


Maryland National Guard Armory
101 Railroad Avenue 

The Elkton Armory is a two-story brick structure with full basement faced with light gray granite, built in 1915. The building’s design imitates a castle, with corner towers flanking two-story curtain walls with irregular window placement. The towers have irregularly placed windows, all with stone lintels and sills except at the first floor where the windows are set into the stone water table. Crenelations with stone caps crown the towers and walls. The Elkton Armory symbolizes the reorganization and expansion of the National Guard system in the 20th century. It derives additional significance from its role as a social center for the community, a function it has served continuously since its construction date. 

World War I Doughboy Monument
101 Railroad Avenue  

Only seven monuments to the men and women who died in the First World War from 1914 to 1918 are known to exist in Maryland. This one, a life-sized Doughboy crafted in white Vermont marble, was originally erected in 1921 in front of the Elkton Court House and moved to its present location in front of the Armory in 1941 after the court house was demolished. The World War I Monument received a much-needed face-lift in 1994.


Trinity Episcopal Church
105 Bridge Street, northwest corner of Main Street

On Friday, November 23, 1832, Bishop Stone consecrated a frame church building on a lot deeded to the Vestry by Samuel Hollingsworth. By the 1860s the congregation had expanded and the present stone Gothic-style Trinity Episcopal Church was erected in 1868. Trinity was separated from North Elk Parish in 1871 and encompassed a wide area of Cecil County, henceforth known as Trinity Parish. It houses an organ built in Malvern, England. The company came to Elkton and built a custom organ for the church. It was the first of its kind in a parish church in the United States. The well-preserved church features a polychromatic combination of dark stone and contrasting red brickwork. It also has a striking, open bell-tower, buttresses, original large door hinges, and a slate roof. 


Hollingsworth Tavern
205-207 West Main Street 

The Hollingsworth Tavern was built circa 1750. During the Revolutionary War, tradition holds that George Washington slept here and 48 hours later, the commanding British general, Lord Howe, in pursuit of Washington’s army after landing his army at the Head of the Elk on August 28, 1777, stayed in the very same room. The brick tavern, front doorway aside, retains much of its exterior appearance from over 250 years ago, especially the prominent keystone lintels over the windows.


First National Bank of North East
139 West Main Street 

Tobias Rudolph, a prominent shipper of grain, built this imposing home with two-story portico (a later addition to the Federal-style core) on one of Elkton’s most visible corners, in the mid-1800s. The English-bond brick work has been painted white. It also has a curved projecting bay, a feature typical of Federal-style design but not frequently seen. In the following century the inside rooms were gutted and it became a branch of the First National Bank of North East.

Elkton Post Office
137 West Main Street 

The first post office established by the Provincial Congress of Maryland was at Annapolis on December 5, 1775. Fourteen post offices were operating by the time Maryland was granted statehood on September 22, 1788, including one at Head of Elk. This handsome post office wasn’t here then, but showed up on Main Street 150 years later. It was constructed in a Federal Revival style of Port Deposit granite blocks. 

Partridge Hall
129 West Main Street 

The present American Legion Hall was the home of Henry Hollingsworth, merchant, legislator and colonel of Elk Battalion of Militia in Revolutionary Way as Commissary for the Eastern Shore. He obtained supplies for the Americans and French allies embarking near here in 1781 on voyage down Elk River and Chesapeake Bay to Virginia, where they engaged the British under Cornwallis. Hollingsworth and other patriots had pledged their fortunes to supply cattle, flour and boats for the armies of Washington, Lafayette and Rochambeau. Hollingsworth built the brick Georgian home in 1768.

158 West Main Street

This mid-19th century hipped roof house, turned restaurant in its latest incarnation, reflects the Greek Revival and Italianate influences of the early Victorian period.

Log House
154 West Main Street 

The somewhat odd appearance of this small structure is due to it being one of the few log buildings remaining in Cecil County, dating to the 1780s. It has been renovated with modern siding.

Pure Oil Company Gas Station
northwest corner of Bow Street and Main Street 

This picturesque cottage-style gas station, built for the Pure Oil Company circa 1935, was typical of the “Domestic” style that dominated gas station architecture in America from the 1920s through the 1930s.   

Howard House
101 West Main Street

The Howard House was built of red brick in 1853 for Jacob H. Howard and H.H. Mitchell on the site of a former frame tavern house. During its 150+ years in existence, this building has experienced many different owners, structural changes, and hosted several important political and civic events. The stuccoed walls happened in 1923, for instance. You can see the historical pictures, dating from 1862, decorating the walls in today’s eatery.    

Cecil County Courthouse
129 East Main Street 

The first courthouse in Elkton was completed in 1792. A one-story brick addition was later constructed to house the Register of Wills, the Clerk of Court and the Sheriff. By the eighteen-eighties, additional space was needed, but the building was hemmed in on every side. The county commissioners had to decide whether to tear down the structure and rebuild or add a third story. The courthouse was enlarged by removing the hipped roof. A mansard third story was added, and a tower was built in front of the building. The tower contained the entrance, a small balcony, a clock, and a semi-onion dome. The tower was topped with a weathervane in the shape of a fish. The courthouse soon became crowded and an effort was made to replace it. In 1935 an act was passed authorizing the county commissioners to spend $5,000 for property on which to build a new courthouse. The site chosen was about 200 yards from the old courthouse. Cornerstone ceremonies took place in May 1939 and building began shortly thereafter. The new courthouse building officially opened on July 26, 1940.

Reverend Duke’s Log House 
129 East Main Street (behind Courthouse, east side of parking lot) 

This building opened as a classical school for boys in 1799 and was the location of the first Episcopal services ever held in Elkton. The cabin was moved from its location on Bow Street in 1970 - without dismantling - to make room for the Elkton Hospital.

Wedding Chapel
142 East Main Street

In the early 20th century, Maryland had no waiting period for issuing marriage licenses, and couples from throughout the Northeast flocked to Elkton―the first county seat south of the State line―where they could be married without delay. Independent wedding chapels lined Main Street. In 1936, the town issued 11,791 marriage licenses. Two years later, the State adopted a 48-hour wait, but the tradition endured. As late as the 1970’s as many as 6,000 couples were wed here in a year. 

Mitchell House
131 East Main Street

This free-standing Georgian townhouse was built in 1769 as the home of Dr. Abraham Mitchell, noted physician from Lancaster, Pennsylvania. During the Revolutionary War he converted the house into a hospital for the use of wounded soldiers of the Continental Army. General Lafayette was a friend of the Mitchell family and visited here. 

Cecil County Historical Society
135 East Main Street 

In 1810, the Elkton Bank was chartered and was the first in the County. In 1816, James Sewell granted the land to the President and Directors of the Elkton Bank of Maryland, who then paid the rent according to the lease which called each year on March 1, for a payment of 3 pounds was due Robert Alexander and his heirs. The Elkton Bank of Maryland failed in 1822 but was followed by others, moving into this building about 1830 with commercial space for a vault and cashier’s office on the first floor and residential quarters for the head cashier above. In the 1890s, architect Levi Cameron completed major renovations to the building. The National Bank of Elkton stayed at this location until 1922 and in 1955 the Cecil County Public Library obtained the building as its home and the Historical Society, that had been incorporated in 1931, was given space, the Howard Room, for its collection. In 1988, the library moved to a new home and the Society occupied a large part of the building.

Kean’s Row
145-147 East Main Street 

This structure is part of tenant housing built of brick laid in Flemish bond along Main Street in the early 19th century known as Kean’s Row. Subsequent owners have clearly had differing ideas on remodeling strategies. 

Wilson & Lidum’s Office
149-151 East Main Street  

Known as Wilson & Lidum’s Office, this nicely proportioned Federal frame building features a dentiled cornice and plain lintels above the windows.

Baker Office Building
153 East Main Street  

If you can ignore the windowless, functional addition to the east, you have a fine three-bay brick Federal building built of brick laid in Flemish bond. It has served much of its existence as a law office.     

Jones-Torbert House    
157 East Main Street 

This mid-19th century house is a fine example of the stylish Victorian houses that marked East Main Street as Elkton’s most affluent and fashionable residential neighborhood. It retains its Second Empire-inspired mansard roof and Italianate detailing such as quoins, window hoods, long windows and bracketed cornice. The stucco has been scored to simulate ashlar blocks. 

First Presbyterian Church
209 East Main Street 

The Presbyterian church organized in Elkton in 1733; this building site came a century later. The present church was rebuilt in 1873 in red brick and contrasting stone trim in the Victorian Gothic style of the day. Details include a large central window and decorative windows and tower decorations. 

215 East Main Street  

This frame clapboard house is marked by a wrought iron porch across the front facade. 

Vanderforce House
220 East Main Street 

A more elaborate example of wrought iron artistry is across the street with this one-story porch with grapevine design. The brick home, laid in stretcher bond with very thin mortar joints, was built in 1853 by William Vanderforce, an editor of the Cecil Whig

Elkton United Methodist Church
219 East Main Street

Francis Asbury, the father of American Methodism, passed through Elkton repeatedly and preached here in 1787 and 1815. In 1799, the congregation was formed at the home of Richard Updegrove on Red Hill. By 1801, meetings were moved to town, and in 1813, a small church was built on East High Street. For nearly 20 years, it was the only house of worship in Elkton. In 1849, the black members organized their own church which became the Providence United Methodist Church. That congregation still worships in the original building. The present brick sanctuary with stucco cover was begun in 1859 and was finished a year later on land donated by sisters Martha Ellis and Jane Torbert. The church was visited by President Ulysses S. Grant while he was calling on his friend and postmaster general, John A.J. Creswell, a Port Deposit resident.  

Elkton House
222 East Main Street 

Essentially a twin of its neighbor at 220, the Elkton House, however, has lost its wrought iron porch.

221-223 East Main Street 

This long brick double dwelling, now apartments, features twin projecting bays flanking a wrought iron porch. The cornice under the mansard roof, pierced by six dormers, is composed of large square white blocks resting on brick brackets.

242 East Main Street

This unusual house blends elements of Dutch Revival (curved front gable), Shingle Style (cladding) and bungalow into essentially a Colonial Revival house.

250 East Main Street 

The remainder of East Main Street features large homes built in Elkton’s gilded age between 1800 and 1910. Collectively, and also within individual buildings, the eclecticism of the period is clearly evident. This house features an excellent two-story Stick Style porch.

Wirt-McCool House
252 East Main Street

This Queen Anne-style house mixes up the patterned shingles and woodwork from the foundation all the way up through the front gable.

Taylor House
254 East Main Street 

This house combines Queen Anne, Shingle Style, and Colonial Revival elements in a unified design, with a shingled exterior, large porch, varied roof lines and architectural details in the dormer and recessed window in the front gable.  

257 East Main Street

This house is a well-maintained remnant of the Italianate (porch) and Second Empire (mansard roof) architectural styles that were popular in Elkton following the Civil War. 

Martha Finley House
259 East Main Street

Once the residence of Miss Martha Finley, a noted Elkton author of the Victorian era, this house is now owned by the Gee Funeral Home. Miss Finley’s residence was described in a book of the times saying, “She has a beautiful residence in the most aristocratic part of the village, surrounded by extensive grounds and a neat hedge fence. In this place much of her best work has been done.”