The town of Princess Anne was created by an act of Maryland’s General Assembly in 1733. Located at a narrow point in the Manokin River known as the “wadeing place,” the land was well-elevated and conveniently suited for the purposes of a centrally located town in Somerset County. Twenty-five acres of David Brown’s “Beckford” plantation were purchased and divided into thirty equal lots with “Bridge Street” (Somerset Avenue) serving as the main north/south thoroughfare. The new town was named in honor of the 24-year old daughter of King George II.

The original courthouse was erected on the corner of Bridge and Broad streets. When it burned in 1832 the court buildings were relocated a block to the south on Prince William street. During the 19th century the town was expanded beyond its 18th century limits with new houses erected in each direction, a testimony to the prosperity of the age. At the time the Manokin River was navigable all the way to town bridge. 

Princess Anne is distinguished by many fine Federal-style dwellings as well as mid-to-late 19th century Victorian houses and early 1900s commercial stock.

Our walking tour will start on the banks of the banks of the Manokin River; where there is a parking area and some off the Town’s oldest history...

WALK DOWN FLURER’S LANE BEHIND THE PARKING LOT.

1.
Nutter’s Purchase
30455 Flurer’s Lane

Christopher Nutter obtained 300 acres along the Manokin River in 1667. A Presbyterian, he hosted services in his house along the river. This frame house was erected circa 1800 as part of a tannery complex. At the time it was common to situate tanneries, and their accompanying noxious fumes, on the outskirts f towns, often by rivers. The cottage is built on a foundation high enough to require steps to reach the front door.  

WALK BACK TO SOMERSET AVENUE TO THE CHURCH AND GRAVEYARD.

2.
Manokin Presbyterian Church
11890 Somerset Avenue

Manokin Presbyterian Church is one of the first organized Presbyterian churches established in America. The first preaching on this ground took place in 1672 when a group of Presbyterians who had settled on the lower Eastern Shore petitioned the Grand Jury of Somerset County for a civil permit to hold services of worship and to have their own minister. It was one of five churches organized by the Reverend Francis Makemie when her arrived from Ireland in 1683. The original church was constructed prior to 1692, the present walls were erected in 1765 and the three-story bell tower was added in 1888.

TURN RIGHT ON SOMERSET AVENUE AND WALK INTO TOWN. 

3.
Election House
Manokin River Park 

This cozy little building was used as a gathering spot and polling place for Town residents in the 1800s. It has taken more than one trip around Princess Anne and was sited here in the 1980s as the centerpiece of the new park and a Visitor Center.

4.
Woolford-Elzey House
11828 Somerset Avenue 

John Woolford, a country doctor, built a simple home on this lot in 1788. Business was brisk enough that by 1798 the property sported a cook house, a smoke house, and a stable and it appeared n the town tax rolls as the most valuable house in Princess Anne. The elaborate portico on the south side of the house is a 19th century addition. The stone walls were thought to have been constructed by Manokin Indians using an ancient technique known as notching to pile up the stones that were probably found as ship’s ballast. When the stone walls were restored in 1976, mortar was necessary.

5.
Charles Jones House
11816 Somerset Avenue, northwest corner of Broad Street

Early deeds indicate a house stood on this prominent corner as early as 1743. Charles Jones obtained the property in 1782 and the house is estimated to date to that time. Jones is thought to have been an innkeeper and may have operated a tavern here. He died broke several years later and this lot was purchased by John Woolford who rented out the house. Renovations in this house reveal 18th century timers, with bark still in place, in the upstairs rooms.

TURN LEFT ON BROAD STREET.

6.
Metropolitan United Methodist Church
30518 Broad Street

In 1842 black members of the St. Andrew’s Church, still bound by slavery, broke away to form their own congregation. Over the decades the group grew prosperous enough to by this site in the 1880s for $400. The cornerstone for the brick Gothic Revival church was laid in 1886 and services began two years later - a symbolically culminating the long struggle some members had endured for the site of the Metropolitan United Methodist Church was once a county jail and slave auction site dating back to the 1700s.

WALK ONE-HALF BLOCK BACK TO SOMERSET AVENUE AND TURN LEFT.

7.
Washington Hotel
11784 Somerset Avenue

This has been the Town’s inn for over 200 years. It was known simply as “The Tavern” until 1857 when it took on the name of George Washington, not for any historic tie to the first president. Stagecoaches departed for the two-day journey to the big city every Monday, Wednesday and Friday. When the railroad arrived, the hotel’s horse and carriage would collect visitors at the train station. Inside travelers found a grand double staircase, one side for ladies, the other side for gents. In case non-gentlemen ascended the staircase it was partitioned to prevent any unplanned glances at the women as they lifted their skirts to negotiate the stairs. The men’s staircase also sported a doublehandrail - the better to grasp on those evenings when one spent longer in the saloon than intended.

8.
Littleton Long Mercantile & Crisfield Law Office
11787 Somerset Avenue 

This is one of the few antebellum commercial buildings to survive in Princess Anne. Littleton Long, a merchant, favored this front-gable, Greek Revival-pediment form for both his house and this store that he built in 1847. Apparently John W. Crisfield, a successful attorney, owned the land and maintained his law office here as well. Over the years the building did service as a bank, a school, a fruit stand, an oyster bar and a pool hall, among others. 

9.
Somerset County Courthouse
30512 Prince William Street, northwest corner of Somerset Avenue 

The first cases to be heard in Princess Anne took place in November, 1742. A wood frame courthouse was erected in Town and stood until 1831 when it burned. The next county courthouse rose on this site in 1833, this time constructed of brick. It stood for 70 years until it was razed to make room for its Georgian Revival replacement. It is said that some of the bricks from the prior house of justice were salvaged and used in the current building that has now entered its second century of duty. 

TURN LEFT ON PRINCE WILLIAM STREET.

10.
Old Presbyterian Church Lecture Hall
30548 Prince William Street, northwest corner of Beechwood Street

This gable-front frame structure was originally used by the Manokin Presbyterian congregation beginning in 1859. In 1910 the Shoreland Literary Society of Princess Anne started the first lending library in Town. Books could be borrowed for a rental fee of two cents each. 

RETURN ONE BLOCK BACK TO SOMERSET AVENUE AND TURN LEFT. 

11.
Mutual Fire Insurance Company
11739 Somerset Avenue 

These were the offices of the Mutual Fire Insurance Company of Somerset and Worcester Counties, housed in an 1884 building that incorporates the rounded Romanesque motifs with the steeply pitched lines of Gothic Revival. The Bank of Somerset began operations here before moving across the street to its own building. The door on the right led to the first floor offices of the bank; the door on the left led up a staircase to the insurance office.

12.
Bank of Somerset
11732 Bank of Somerset 

The Bank of Somerset opened this one-story Neoclassical vault in 1903. It was constructed with yellow Italian brick on a granite foundation. Its wide central double door with semi-circular fanlight has stone trim with an ogee-carved keystone, set in a pedimented pavilion flanked by pilasters.

TURN LEFT ON WASHINGTON STREET.

13.
John W. Crisfield House
30556 Washington Street 

John W. Crisfield built this Late Federal/Greek Revival house a few hundred feet away on Somerset Avenue in 1852. When the Standard Oil Company of New Jersey wanted to build a gas station on the main drag through town in 1927 the owners of this house moved it off main street.

John Crisfield was a lawyer and United States Senator whose main interest for many years was bringing railroad service to the lower Eastern Shore. Earlier schemes to bring the iron horse down the peninsula had failed but Crisfield, as president of the Eastern Shore Railroad, was relentless, Even the Civil War sidetracked him only temporarily. In 1868 the railroad was finally extended to the sleep town of Somers Cove on Tangiers Sound. Not only did area farmers benefit but almost overnight Somers Cove became the seafood capital of America, shipping oysters and crabs by the trainload. A grateful citizenry rechristened the town, “Crisfield.” It was small consolation to John W., who went bankrupt in 1876.

14.
Anna L. Haines House
30560 Washington Street 

This T-shaped townhome erected in 1909 is one of the few brick houses in Princess Anne. Anna Haines patterned her home after dwellings she knew in Philadelphia. Two-story bay windows distinguish both street elevations and the roof is covered with slate shingles. 

TURN LEFT ON BEECHWOOD STREET. 

15.
Colonel George Handy House
11719 Beechwood Street 

This crisp, well-preserved Federal-style house was constructed in 1805 by George Handy. Handy enlisted in the Continental Army at the age of 18 and served from the beginning to the end of the American Revolution. A close friend of Alexander Hamilton and a colonel on the staff of General Light Horse Harry Lee, Handy distinguished himself at the storming of Augusta. After the war, in 1787, the 31-year old Handy married 16-year old Elizabeth Wilson. The union cause a bit of a scandal and the couple were forced to seek wedded bliss in South Carolina. Eventually they returned to Princess Anne where Elizabeth and George had 12 children. Handy was elected sheriff in 1797 so apparently all was forgotten and forgiven.  

16. 
The Laura House
11728 Beechwood Street

This T-plan dwelling from 1905 is trimmed with modest Victorian features including the turned-post front porch.

RETRACE YOUR STEPS TO SOMERSET AVENUE AND TURN LEFT.

17.
Boxwood Garden
southeast corner of Somerset Avenue and Washington Street 

The French parterre boxwood garden has provided a green respite in the center of town for over 150 years. Started by the Handy family, the tradition of caring for the garden has continued through successive owners down to the present day. 

18.
General George Handy House
11695 Somerset Avenue

The General George Handy house carries an unusual degree of architectural and historical significance in Princess Anne. Built around 1845, this townhouse was initially only one room deep and covered by a hip roof. During the third quarter of the 19th century the man house was extensively reworked with a rebuilding of the roof and remodeling the first floor interior. Despite the extensive Victorian alterations, the house retains large portions of its late Federal woodwork on the second floor and in the rear service wing. Thus the house displays fine examples of craftsmanship from the two major stylistic periods found in Princess Anne.   

19.
Joshua W. Miles House
11673 Somerset Avenue

Joshua Miles was president of the Bank of Somerset but this contribution to the Princess Anne streetscape is anything but conservative. The exuberant Queen Anne house was built in 1890; its dominating feature is a three-story octagonal tower. The design has been attributed to Baltimore architect Jackson C. Gott. 

20.
William W. Johnston House
11653 Somerset Avenue 

William Johnston was a Princess Anne merchant and also owned a gristmill and a sawmill. When he built this finely-detailed late Federal home in 1835, this was the southern edge of town. Desiring to face his customers and the town center, Johnston built his home facing north. When the town kept growing down Somerset Avenue, it left the orientation of the house appearing odd. Although it doesn’t look out over the street, the double door is a particularly excellent Federal-era entrance.

TURN RIGHT AT ANTIOCH AVENUE. TURN RIGHT AT CHURCH STREET.  

21.
Littleton Long House
11696 Church Street

Little Long came from humble beginnings - he was indentured as a bootmaker for seven years beginning at the age of 14 - but married into money when he won the hand of Ann Costen. Her family heartily disapproved but the couple married in 1821 anyway and were known around town as the Runaway Match. The Longs built this Greek Revival frame house in 1829. Long began his post-marriage career as a merchant and then earned a law degree and entered state politics. Littleton and Ann raised eight children and one of their sons was credited as being the first Westerner to discover the source of the Nile River.  

22.
St. Andrew’s Episcopal Church
11700 Church Street 

The first congregation representing the Church of England met near the river as a chapel-of-ease in the 1600s. In 1773 the first church was completed with money raised by selling tons of tobacco (it took 128,000 pounds to buy this land) and the congregation has operated continuously ever since. The church was consecrated as St. Andrew’s in 1845 and the tower was added in 1859. The differing brickwork tells the tale of the sanctuary’s growth.

TURN LEFT ON PRINCE WILLIAM STREET. 

23.
C.H. Hayman House
30491 Prince William Street

Legend has it that when Charles Hayman knew he was going to be building this house in 189 he opened a hardware store a block away so that he would be certain to have the finest materials available. The rambling Queen Anne/Colonial Revival design features a wealth of Victorian detail including Tuscan porch columns and urns perched on the balustrade posts. In the Colonial Revival tradition, the house is perfectly symmetrical.

24.
Dougherty House
30466 Prince William Street 

This house was clearly built in two different eras. The beginning block (west side) dates to the 1830s and is an austere Greek Revival design. After the Doughertys purchased the home after the Civil War they added the more light-hearted, bracketed eastern block.  

25.
Judge Levin T.H. Irving House
30459 Prince William Street  

This 1850s house was cleaved from its northern neighbor, Mariner’s Cott.

26.
Teackle Gatehouse
30466 Prince William Street 

Originally access to the 10-acre Teackletonia was through a pair of twinned gatehouses facing the town. Both free servants and slaves lived inside the iron-gated homes. After Littleton Teackle’s financial empire collapsed the northern gatehouse here was the last thing he owned; he lived here for years. 

27.
Fontaine-Fitzgerald House
30459 Prince William Street 

This pure Greek Revival frame house dates to the early 1850s; the two-story portico and side-lighted doorway entrances are original.

28.
Francis Barnes House
30449 Prince William Street 

This is a well-designed example of the mid-19th century bracketed house crafted by master builder Seth D. Venables. Like all the surrounding houses, the Barnes House was built on the remnants of the Teackle estate.

29.
Rufus Parsons House
30448 Prince William Street  

Rufus Parson was a farmer and promoter of the Eastern Shore Railroad. He built this handsome Greek Revival house in 1858, setting it on a high foundation to give it an impressive stature and provide room for a basement. The Parsons sold the house in 1861 for $3,300.

30.
Teackle Mansion
11736 Mansion Street 

Littleton Dennis Teackle figures prominently in the history of the lower Eastern Shore of Maryland on many levels -- as a merchant, entrepreneur, and (in later years) statesman. Born in Accomack County, Virginia to one of the wealthiest gentry families on the Eastern Shore, L. D. Teackle moved to Somerset County, Md. with his expectant wife, Elizabeth Upshur, in 1801. He followed in the footsteps of his successful father, John Teackle, by establishing a trans-Atlantic merchant enterprise in a family partnership. Teackle began work on what would become a 10,000-square-foot landmark on the Eastern Shore following a grand tour of England and Scotland in 1799-1800. It is surmised that he modeled his home on a Scottish manor house he saw on his travels. The couple called it Teackletonia, a name intended to differentiate their house from his uncle’s Beckford mansion sitting a few hundred yards to the southwest. But the optimism L.D. Teackle had for the economic outlook was immediately met with complications: disastrous weather in 1802-04 that caused extensive loss of crops, the beginning of the Napoleonic wars in 1803 that disrupted trans-Atlantic trade, the Federal government’s Non-Importation Act, the ensuing Jeffersonian Embargo in 1807, and several years of war with Great Britain, all took a tremendous toll on the Teackles’ success. It would be 15 years before the hyphens and wings would be completed, enlarging the house to its full, five-part size. Despite Teackle’s varied business pursuits, he never maintained financial stability. In 1839, four years after his wife’s death, he and his only daughter, Elizabeth Anne Upshur Teackle Quinby, sold the Mansion. Several years later, after selling the remainder of his property, Littleton Teackle moved to Baltimore, where he died alone in a hotel room in 1848. In the century following Teackle’s death, the Mansion and its adjacent property were separated into three deeds. Owned by several local families, the Mansion was gradually divided into apartments and in the 1930s and 1940s was primarily occupied by tenants. In the 1950s, a small number of Princess Anne residents founded Olde Princess Anne Days, Inc. to raise funds for the purchase and restoration of the south and central sections. The north wing was purchased around the same time by the Somerset County Historical Society. The two groups merged in May 2000, bringing single ownership to the Mansion for the first time since before the Civil War.

TURN RIGHT ON MANSION STREET. 

31.
Seth Venables House
11748 Mansion Street

Seth Venables, a master carpenter, built many Princess Anne houses. This one he built for himself, in 1852. He called it Simplicity. These were some of the last handmade houses in Town, being built before the railroad brought mass-produced goods and pre-cut lumber to the builders. 

TURN RIGHT AT THE END OF ROAD ONTO MANOKIN STREET AND TURN LEFT ON BECKFORD AVENUE.  

32.
Police Headquarters - “The Grey Eagle”
11780 Beckford Avenue

The granite Somerset County Jail was built in 1857. It was burned by prisoners in 1902 but rebuilt with three new Bessemer steel cages. The jail cruised into its second century of service before it was considered no longer fit for use in 1976 and closed. A restoration in 2008 has transformed the “Grey Eagle” into a police precinct building.

TURN RIGHT ON BROAD STREET. 

33.
William Geddes House
11790 Church Street 

This is the oldest documented house in Princess Anne, going back to at least 1755 when it was owned by William Geddes, a merchant and shipper of wheat. Geddes would obtain a degree of immortality two decades later when, on May 23, 1774, “a group of Chestertown citizens undisguised and in broad daylight” boarded the brigantine Geddes, owned by then-Custom Collector William Geddes, and threw its cargo of tea into the Chester River. The town then became a faithful supplier of provisions to the town f Boston, then suffering under the Boston Port Act. Chestertown remembers its Revolutionary heritage during the Chestertown Tea Party Festival held during the Memorial Day weekend. 

CONTINUE ON BROAD STREET TO SOMERSET AVENUE AND TURN LEFT, CROSSING THE MANOKIN RIVER TO THE TOUR STARTING POINT.