The research for this tour is from History of Portsmouth, Virginia by Mildred Holladay & Dean Burgess as well as interviews with Mr. Burgess himself. If you would like to read and enjoy more stories about Olde Towne Mr. Burgess’ book may be purchased at the Portsmouth Arts & Cultural Center on High Street.
As you stroll through the largest collection of 18th and 19th century historic homes between Alexandria and Charleston, make sure to watch your step as many of the bricks are not level. When you see the word “circa” or “c.” on historic signs that is Latin for “about”.
Dean Burgess, local historian explained in his book, “The town of Portsmouth entered upon its municipal existence on February 27, 1752. It was laid out like an English country town with broad streets alternating with narrow ones in a grid pattern. It was also laid off in squares and is one of the few American cities to retain the original names of its blocks. One explanation for this layout is that the elegant houses stood on the broad streets and the homes of the artisans and lesser lights on the narrow streets.”
Since Olde Towne has over 200 period homes to enjoy with some unique and amazing architecture, this tour could become lengthy. For your convenience, directions are provided for 3 different length loops. You can choose to walk 0.6 mile, a little over a mile, or close to 2 miles with directions back to the parking garage at each point.
Our tour begins at the Middle Street Garage on the corner of Middle and London Streets
1. Red Lion Tavern
Cross London Street and turn right toward the waterfront.
Your first stop is Red Lion Tavern at 218-220 London Street
Built in the mid-eighteenth century as a tavern for soldiers and sailors, old menus and a cockfighting pit were discovered in the cellar during renovations. At the time, this was a very popular sport done openly and aboveboard aided and abetted by the church. The owner of the home, Mr. John Cornelius Portlock Edwards, hosted the Grand Duke Alexis of Russia in 1877 and even procured a main of cocks for his special pleasure. A very colorful character, he arranged his own funeral which was held on January 21, 1896 at 2 am amidst the shrieks and howls of a drunken mob of over 500 people carrying torches and lanterns. He was buried standing up beside his two favorite horses and four dogs. Following the last prayer, the grave was bricked up, and the crowd left for refreshments and a cock fight.
2. Pass House
Continuing our walk down London Street to Crawford Street, you will see the Pass House built in 1841.
With 24 rooms covering 5,300 sq. feet, this Greek Revival-style home was built by local attorney James Murdaugh. Though the Murdaughs temporarily relocated after the Civil War, the family did ultimately return. In 1895, Ellie Murdaugh married John Archer Lejeune in the grand foyer. Lejeune played a critical role in re-organizing the United States Marines in the 1920s, and North Carolina’s Camp Lejeune is named in his honor. During the Civil War, the basement of the house was used as an office for the provost-marshal. It was here that the Union occupation issued passes to cross the ferry to Norfolk. Citizens had to swear allegiance to the Union to be permitted to leave the city. This house is an excellent example of an English basement house.
3. Cassell-McRae House
Cross Crawford Street and continue on London Street to 108, the Cassell-McRae House, which was built around 1829.
This home features a double sunburst window as well as a hand carved arched doorway. The pineapples on the gate posts are a colonial symbol of hospitality. According to legend, a ship captain would bring pineapples back from the Caribbean and spear one on the fence post outside his home to let his friends know he had returned safely from his voyage. The pineapple was an invitation to visit, share a meal, and hear tales of his voyage. Mark Twain stayed here in 1907 when he was a guest speaker at the Jamestown Exposition.
4. Benthall-Brooks Row
Walk back to Crawford and turn right to see Benthall-Brooks Row found at 415-421 Crawford Street.
These English basement homes date back to the 1840s. All three brick houses were built by a sea captain named Benthall. Captain Benthall would build one ship, send it to the Caribbean where he would sell it for rum, import the rum, and sell it to pay the crews, sailors, and shipwrights, and still have enough money left to build another ship.
On 421 Crawford Street you will see a fire mark. For 150 years American insurance companies issued them. Fire marks served many purposes, but the main reason in America is quite simply, a fire mark was an advertising sign that the property was insured. Both the insurance company and the insured benefited from displaying a fire mark. It may have been the only evidence of insurance, after the insurance policy burned with all the other contents in the house. Perhaps, a mark simply stated to others that the person had enough good sense to purchase insurance. Each insurance company had its own design and you will see several different ones throughout Olde Towne.
5. 419 Crawford Street
Notice the carriage block that is in front of the home at 419 Crawford Street. It is also known as a mounting block and was used to get in and out of a carriage.
6. 411 Crawford Street
You will notice the last house at 411 Crawford is made of wood. It was built by the first baker in Portsmouth in 1840. After a huge fire that burned nearly every house on Crawford from High Street to Glasgow, as well as all houses east to the water and the town market, an ordinance was passed that divided the town into fire districts and only stone or brick buildings could be built in this part of the city. You can only imagine the scene when all able men and boys in the city both black and white, formed 2 lines from the Elizabeth River. One line passed the empty leather buckets and the other line the full ones. These brave and dedicated men worked their hearts out knowing that there was little hope for these doomed structures.
7. Lafayette Park
Continue down Crawford and you will see the Lafayette Arch at the corner of Glasgow and Crawford Streets.
When the U.S. celebrated its 200th anniversary, the arch was dedicated to all who have lived or died for freedom. It was inspired by an arch erected in Portsmouth in 1824 to honor the Marquis de Lafayette’s visit to the city. The lion’s head came from the demolished American National Bank Building on High Street. If you walk into the park, you will see a memorial to the Shopmates who died in World War I and World War II, as well as one to the Congressional Medal Of Honor Recipients from Portsmouth.
8. 205 Glasgow Street
Continue your tour from the Lafayette Arch. You are now at the corner of Crawford and Glasgow Streets. Cross Crawford Street.
Directly in front of you is 205 Glasgow Street which is the last of the Irish row homes. The Irish immigrated to the United States around 1800 and then it was required that they relinquished their allegiance to the Queen when they came to America. The remaining house has a walk-in fireplace and a 24-inch stairway leading to its loft, in the style of cottages in Ireland.
9. 215 Glasgow Street
Continue down to 215 Glasgow where the first floor was built around 1830, but in 1870 the original city market was placed on top of the existing house. Notice that the upper and lower windows don’t line up. The homeowners can still see the market stall numbers on the second-floor beams. Standing in front of the door, look up to the second-floor window and you will notice the “Philadelphia busybody” invented by Benjamin Franklin. This set of mirrors works like a periscope to let the homeowner look out of the window and see who is coming down the street, or possibly watch for the carriage to arrive. This home features the original windows and shutters.
Next, notice the lantern to the left of the house. These street lights were originally gas lanterns bought from Manchester, England in 1967. They were placed in front of the homes with architectural merit when Olde Towne was placed on the National Register of Historic Places. The cross piece was used by the wick-trimmer to lean his ladder. You will also notice a fire mark as well as a boot scraper by the door so visitors don’t track mud into the home.
10. Spanish American War Monument
Next, return the way you came and go back to Crawford Street and turn left.
Walk one block and look across Crawford Street to the median and you will see the Spanish American War monument which commemorates the Portsmouth men who served in Cuba and the Philippines during the Spanish American War 1898-1902. This monument is one of at one least fifty bronze castings of American infantrymen across the country. The Hiker was sculpted in 1905 by Theo Alice Ruggles Kitson, the first woman to be admitted to the National Sculpture Society.
The statue was erected by the citizens of Portsmouth and Norfolk County on May 23, 1942.
11. Grice-Neeley House
Cross North Street and on the corner at 202 North you will see the Grice-Neeley House which was built around 1820.
This English Basement house has many Greek revival features including the columns, pilasters, and six-over-six window panes. The ironwork on the North Street side of this house was found in the basement during restoration and is original. The white marble step to the backyard is a stone from the grave of a boy who died here in the 1870s. The willow oak on the stone symbolizes the brevity of life. This home also displays a fire mark. Frank Grice and his collaborator Captain Neely designed and built the steam frigate Powhatan which was Admiral Perry’s flagship when he opened the ports in Japan. Since it was the first steam powered ship there, the Japanese said that the Americans had brought a dragon into the harbor!
12. 216 North Street
Continue down to 216 North Street on the right. Notice the four houses in a row and the difference in the architecture for each demonstrating the great variety of architectural styles in Olde Towne.
13. 218 North Street
You will see that 218 North Street is a fascinating example of High Victorian architecture. Note the stained glass fan light (fan-shaped window) on the third floor decorated with plaster wreaths, the stained glass on the second floor, as well as the interesting curved porch, and basement entry. The capitals on the columns are from the Ionic order.
14. Hill House
Look directly across the street at 221 North, you will see the Hill House built in 1825 by Colonel John Thompson.
It is a four-story English basement house. This branch of the Hill family died out in the 1940s leaving the house with all of its furnishings (even clothes in the closets) to the Portsmouth Historical Society. Most historical houses are furnished with period pieces. It is quite unusual to have one where all of the furnishings are original.
Guided Tours are $5 and are available Wednesday and Saturday 12-3 from May through December or by appointment. For tour information call 393-0241.
15. Washington Reed House
Next to the Hill House you will notice a large pale yellow brick home built in the 1790s. This fine example of Georgian-style architecture is the Washington Reed House. As you walk by, look up and note the beautiful dentil ridge at the roofline and the cornices above each window. The fan light on the north side of the attic is in the pediment gable. You will also notice the street signs are attached to the corner of the house.
16. Town Pumps
You are now at the corner of Middle and North Streets
In the center of this intersection was the location of one of the town pumps until the days of city water. These street pumps furnished a meager amount of brackish water, while wells supplied better water. Those who had no wells caught rainwater in a barrel. This brand of water was better for drinking than the well water. Women would never be seen on the street unescorted, but teenage girls and boys could fetch water for the family. Many romances and marriages were formed from rendezvous at the pump.
17. 300 North Street
On your right across Middle Street is the Leigh-Cox House at 300 North Street.
A classical Georgian style home, it was built in 1800 by Dr. William Leigh, a Revolutionary War veteran. He owned a distillery at Gosport with four stills that produced 300 gallons of whiskey a year. He later sold the house to Virginia Militia General John Hodges. Hodges later served as Portsmouth’s Postmaster, and the Hodges Ferry section of Portsmouth is named after another piece of his property.
18. 334 Middle Street
Just behind his house at 334 Middle Street was the home of the owner of the town’s largest bank at the outbreak of the Civil War. He refused to divulge to the occupying forces who had money in the bank and was imprisoned at Fortress Monroe for the duration of the war.
19. Macon House
Cross Middle Street and you will find the blue, brick Macon House built in 1830 with the attached, yellow Macon Hotel facing North Street which was built in 1851. If you walk down North beside the former hotel, you can see the Path of History placard with more information. The opposite side of North Street had not yet been developed and had an attractive view of the Elizabeth River. Imagine staying here and enjoying a beautiful beach view. The Macon House was well-known as a resort hotel and was beautifully furnished and equipped with every convenience. There was a bathing house near the beach for the pleasure of the hotel guests, and the hotel also had bathing machines which were little horse-drawn houses on wheels with an open floor so ladies could be taken out into the river and bathe without being seen.
Many women with their attendants visited, as well as visiting sea captains from around the world. Gentlemen could also play billiards all evening for $0.25. It was so luxurious that the British Consult chose to live here. During the Civil War, the Macon House was filled with Confederate officers and their families. After the Confederate evacuation, it became a Union hospital. The signatures of wounded soldiers remain carved in the floorboards. The attached house facing Middle Street was the private residence of the hotel proprietor. During the War it was occupied by the officers in charge of the hospital.
20. Borum House
Return to the corner of Middle and North Streets. Turn right and walk south down Middle Street and look across at 355 Middle, the Borum House built in 1867.
You will notice the verandas feature fretwork in the New Orleans style. By 1867, many foot-powered and hand-cranked scroll saws were available in the US. The evolution of the scroll saw is linked to the rise in popularity of fretwork.
21. Nash-Gil House
When you reach 370 Middle, you will see the Nash-Gil House built in 1880 which is a wonderful example of late Gothic Revival architecture, sometimes referred to as “Steamboat Gothic”. Once again this style of “gingerbread” became popular after the invention of the scroll saw. Notice the interesting shapes of the windows and the slate roof. For more information see the Path of History placard by the home. If you are feeling tired, enjoy one of the benches in Red Lion Park before you continue your tour.
22. Ball-Nivison House
Cross Middle Street toward the playground and continue walking south.
Next on your left you will find the Ball-Nivison House at 417 Middle Street which was built in 1752 even though the Bill of Sale indicates that it was sold in 1784.
The house was built by John Nivison and was originally located on Crawford Street. Moved to its current location to make way for the Seaboard Air Line Railroad in 1869, the house was used as a barracks during the War of 1812. The home also entertained the Marquis de Lafayette in 1824 and President Andrew Jackson in 1833.
When Andrew Jackson and his cabinet came to Portsmouth at the opening of the Gosport Dry Dock in 1833, they stayed here. Mr. Ebenezer Thompson, who was at that time about ten years old, was employed to keep the men who were working on the dock supplied with drinking water. He carried a bucket and dipper. On the day of the President’s visit, he was stopped by a tall gentleman who asked for a drink of water. Seeing that this wasn’t a workman, he replied, “ I haven’t the time, Sir; I’m hired by the government to wait on its employees.” “Then, my lad, I’m entitled to a drink. I am employed by the government as its President, Andrew Jackson at your service.” Mr. Thompson was still an employee a the Navy Yard at age 90 and could still remember that day vividly. For more information on the home and the interesting people who have visited here, you can read the Historic Marker.
23. The Colonial
Across the street from the Ball House is 414 Middle Street, the Colonial, a large building with a very interesting history. This Greek revival building was built in 1835 and was originally a two-story structure that was the Odd Fellows’ Hall. The third floor was added in 1901 in a very unusual way. The entire roof with its massive cornice was lifted on supports, and the new second story was built under it. The Doric columns of the portico were made higher in the same way. These three-story pillars are solid brick covered with stucco. The triangular section above the pillars is an excellent example of a classical pediment. The Odd Fellows was a national fraternal order. It may have gotten its peculiar name from the fact it included members of the working class who otherwise were not eligible for membership in such exclusive clubs and, therefore, were “odd”.
24. Plaque in honor of William “Billy” Flora
Continue down Middle Street then cross London, and you will once again see the Middle Street Garage.
In front of the garage is a plaque in honor of William “Billy” Flora, a distinguished African-American citizen. His heroic service at the Battle of Great Bridge during the American Revolution was critical in defeating the British. He held back Governor Dunmore’s Ethiopian Brigade at the Bridge, which they attempted to cross three times and were driven back by his fire. This delayed the British just long enough for the militia to draw up before the bridge and to drive the enemy forces back to Portsmouth. Flora was a free black, but his wife was not. He purchased her out of slavery, but unfortunately the baby she was carrying having been conceived when his wife was a slave, was still a slave, and so he had to then buy his daughter out of slavery when she was born. His livery stable stood on the corner of London and Middle Streets.
0.6 Mile Marker
There are many more wonderful stories and beautiful houses, but if you feel you have done enough walking for the day, you can return to your car at this point. You have walked 0.6 mile.
If you need coffee or maybe something to eat before you continue your tour, walk 2 blocks down Middle Street to High Street for a restaurant or the locals’ favorite coffee shop which stands where Benedict Arnold’s headquarters stood when he was the commander of all British forces in the Commonwealth during the American Revolution. (Despite being a turncoat, when he died in London, his wife complied with his final wishes to be buried in his American general’s uniform.)
25. 320 London Street
To continue your walk through history, cross Middle Street and keep walking until you see 320 London across the street on the right.
This interesting home was built in 1886 by a gentleman named John Neeley who owned a lumberyard. When building the house he decided to include every fashionable architectural detail of the day. You will notice a cupola, tower, bay window, and stained glass windows.
26. Court Street Baptist Church
As you approach the next intersection at Court Street, you will see Court Street Baptist Church which was burned down and rebuilt of pink granite quarried in Salisbury, N.C. in 1901. This church is one of only two Baptist churches in this exuberant Romanesque Revival style in the nation. The other is in Tennessee. The stained glass is also exceptional in its design, with yellow and shocking pink predominating. The windows go up the stairwells to the towers. When hit by full sunlight this creates a golden glow in the church that is quite unique.
If you would like a tour of the sanctuary, please stop in the office from 8-4 Monday through Friday, and someone will gladly assist you.
27. 430 Court Street
Cross Court Street and stop at the Italianate home on the corner at 430 Court. This house and the one across London were built by the Parkers, two Catholic brothers who had 28 children between them. If you take a few steps down the side of the home, you will notice that it has had three different brick fronts. The house was originally built in 1830 in the Federalist style of the time. Notice the porous brick walls built with the Flemish-bond technique. Around 1860, the structure was given a new facade and then finally in 1917 the current Italianate front was added. During this time, it was important to keep up with current style. If you look up you will notice the Xs on the side wall. These are ends of masonry ties that hold the joists in place. During renovations, a cannon ball was found embedded in the attic.
28. 420 Court Street
Despite research, there seems to be no reason why the streets running east and west in Olde Towne have two 300 blocks and two 400 blocks. This does tend to confuse visitors. So when you cross London Street and continue down Court, you are still in the 400 block.
The home at 420 Court was built in 1874 by Joseph Parker and is an excellent example of Victorian architecture. The residence features a sacred heart above the doorway which was a symbol of his Catholic faith. The home had 14-foot ceilings and had a chapel above the foyer where the family worshiped. As you stroll down Court Street, notice how wide the street is compared to the ones you walked on earlier indicating this was a street for the gentry.
29. 408 Court Street
Keep walking and at 408 Court Street you will see a wonderful example of handblown glass windows. The window would start as a ball of molten glass at the end of a blowpipe. It would be blown until it formed an elongated tube of the desired length and diameter. The ends would be removed forming a cylinder, which was then cooled. The cylinder would be scored down the length, reheated and flattened to form the glass for windows.
30. 401 Court Street
When you reach the corner at Glasgow, look across the street at 401 Court Street.
During the gold rush in California in 1849 and 1850, when people were clamoring for houses there, several cities undertook to send them pre-fabricated homes like this type of building. A company to build such houses was formed here. The necessary parts for constructing a house were cut and fitted ready to be set up. These parts were numbered then bundled and shipped to California by sailing vessels around South America. The Niemeyer House is one of two “ready to put up houses” still standing in Portsmouth.
31. 400 Court Street
On your left at 400 Court Street is an English Basement house that belonged to the British Naval Attache before the American Revolution. This and many other homes became Mom & Pop groceries up until the 1960s. Notice the brick pattern in front of the house and you can see where the original stairs went to the second story living quarters.
32. 370 Court Street
When you cross Glasgow, you will see 370 Court Street which was built in 1906. A receipt was found for the granite showing that it was purchased from Court Street Baptist Church. The architecture on this home is once again Romanesque Revival. The gorgeous cut glass front doors were found wrapped in newspaper in the basement and restored by the previous owners.
33. 344 Court Street
Continue down Court Street and cross North Street to 344 Court Street.
This was the home of Thomas Hume, the first Superintendent of Schools for the city and the minister of Court Street Baptist Church. The introduction of stronger plate glass from the 1830’s allowed the use of larger glass panes, offering improved ventilation and natural light, as well as improving views to the outside.
34. Trinity Church Rectory
Your next stop is 340 Court Street, the Trinity Church Rectory built in 1826 by Thomas Hume. This is a classic example of an English basement house. You might notice that the “basement” is actually the first of four floors. The basement was used for family rooms or possibly slave quarters. The second floor was where the family entertained guests. The third floor housed the adult bedrooms and the fourth floor space was usually less than 6 feet tall with one-quarter sized windows and used for children’s bedrooms. The Parish was pressed for money during the depression and sold the interior paneling to the Colonial Williamsburg Foundation during their restoration.
35. 336 Court Street
A few steps away one of the local doctors lived at 336 Court Street. If you look just to the right side of the door you will notice an important invention of the time. If a person had an emergency after hours, they would go to the doctor’s house and yell in the “speaking tube” which carried the sound to his bedroom. He could listen to the problem and determine if it was worth getting out of bed for or could wait until morning. This home also has a fire mark.
36. 328 Court Street
Next you will pass a beautiful brick home at 328 Court Street. Rather large and elaborate for a Portsmouth townhouse, it is the only house in the city that displays the Art Nouveau style, then in fashion. The architect was Charles Cassel who also designed St. John’s Church on Washington Street. Notice the stunning carved capitals on top of the columns. This house is one of the few still owned by the family which built it.
37. 318 Court Street
Continue to stroll down Court Street to 318 Court where you will see an architectural feature which is often seen on Victorian homes, a witch’s cap. Notice the original slate roof.
38. 316 Court Street
The house next door at 316 Court features beautiful stone work and Ionic capitals on the columns.
39. 300 Court Street
When you reach Waverly Blvd. you are at 300 Court which is a beautiful Queen Anne Victorian home. The pediment is an outstanding example of turn of the century architecture. The small structure beside it was the office for the doctor who lived in the house. This home does provide a wonderful view of Crawford Bay and the Norfolk skyline. Also there is a bench handy if you need to sit a few minutes before continuing.
40. Swimming Point Walk
Across Crawford Street, you will see Swimming Point Walk. This sidewalk allows pedestrian access to the Swimming Point neighborhood, best known for the Dale-Reed House (200 Swimming Point), the oldest house in the city. Colonel William Crawford built this Georgian-style house in 1732 for his plantation overseer Daniel Dale. It included 100 acres of plantation and is the birthplace of Commodore Richard Dale, a famous American Revolutionary naval officer.
41. 315 Court Street
Cross Court Street and return on the other side.
Your next stop is 315 Court Street, a Classic Revival house designed by Pierre L’Enfant who also drew the street plan for Washington D.C. Originally, this home was to be built for the Federal government to be used as officer’s quarters, but it was considered too ornate. William Peters got the plans and built the house in 1859. When it was constructed, the north portico overlooked a garden sloping down to the river.
In the Civil War, when Portsmouth was occupied by Union soldiers, this dwelling was confiscated by Union General Benjamin Butler for his headquarters in 1862. He was nicknamed “Spoons” Butler because of the strange disappearance of silverware whenever he inspected local homes. Later when Butler ran for President on the Greenback ticket he hung a banner that said “Vote for the Hero of Five Forks” and someone wrote under it “and God knows how many spoons!” The home was sold in 1910 to John Porter, the grandson of the naval architect responsible for the Confederate ironclad Virginia. It has been in the Porter family ever since.
42. 323 Court Street
Passing 323 Court, you will see another home where the wrought iron railings are an excellent example of the New Orleans influence on architecture of the time.
43. 326 North Street
Court Street offers a variety of architectural styles and features – too many to mention them all, but enjoy the beauty as you continue to North Street. At the corner, you will see 326 North Street, The Bain House. The house sits on the original site of General Cornwallis’s Portsmouth headquarters. Cornwallis and his troops sailed from Portsmouth to Yorktown to fight the final battle of the American Revolution. William Armistead offered his services to Lafayette and brought his slave, James with him. When Lafayette realized how intelligent James was, he recruited him as a spy. First, he was at Benedict Arnold’s headquarters, and then later here after Arnold departed. Cornwallis also saw his usefulness as a spy and sent him to spy on Lafayette which allowed this patriot to pass back and forth between the lines carrying intelligence to Lafayette and hoodwinking Cornwallis. Lafayette embraced Armistead and publicly told his story and Armistead added Lafayette to his name. He later won his freedom using a letter from Lafayette about his service.
The Bain House was built in 1830 by Antonio Bilisoly. The Bain brothers purchased the home just after the Civil War. They were bankers and in 1885, were involved in the biggest bank fraud scheme in Portsmouth history.
44. Elk’s Lodge
Cross North Street, and you are at 329 North, the former Elk’s Lodge. This excellent example of Romanesque Revival architecture was built in 1892 by Mr. Beverly Armistead, president of the Bank of Portsmouth. This style of home is sometimes called a “General Grant Victorian”. Identifying features of this architectural style are the round arches over thick cavernous entryways and window openings. The tall arched windows and curved glass were intended to give a shadowed effect inside. The turrets, finial, and decorative shingles are also excellent examples of the common features of this type of architecture. The home was converted to the Benevolent and Protective Order of Elks Lodge 82 and later known locally as Dr. Madblood’s Castle, the imaginary home for the television show Dr. Madblood’s Movie. For more information about the history of this grand building, see the Path of History placard facing Court Street.
45. The Grice House
Walk on North Street passing the front porch of the Elk’s Lodge and when you look across the street you will see another amazing home at 318 North, the Grice House.
Dr. Grice built this handsome house set back from the street for his new bride who was the daughter of the Bishop of Southern Virginia. He proposed the city create a Health Department, which seemed an outlandish idea to the town council. Finally Grice opened his own health department for the city. Patients entered from the little side porch which still can be seen on Gaskins Lane. This house has a widow’s walk on the roof. It was where the wives of sailors would watch for their husband’s ship to enter the port. You will also notice there is a hitching post in front of the residence.
46. 316 North Street
Continue down the street and cross over North Street at Gaskins Lane to 316 North. You will see the residence of James Gaskins, the town’s first silversmith and a Revolutionary War veteran. The Path of History placard gives more details about this home.
A little over a mile!
Although there are many more interesting stories and historic homes to enjoy, if you are ready to leave, continue down North past the Macon Hotel and Civil War Hospital and turn right on Middle Street. Keep walking straight and you will be back to your starting point at the Middle Street Garage.
If you decide to stop here, you will have walked a little over a mile.
47. 417-419 North Street
If you would like to continue your historic walk, turn around and walk back down North Street crossing Court Street. On the left at 417-419 North, you will see two beautiful brownstone Romanesque homes built in 1916. Notice the bowed glass and the gargoyle on the third floor as well as the fire mark. At one time Jim and Tammy Faye Baker lived here in 419.
48. 424 North Street
As you pass 424 North Street on the right, notice the capitals on the columns are from the Corinthian order and the decorations on the roof are snow guards or snow brakes.
49. 497 North Street
At the end of the block cross North Street to your left, and you are at 497 North where you will see a mermaid statue. This lovely Queen Anne Victorian home was built in 1898 by Dr. Parrish.
50. Watts House
Diagonally across the street, you will see the Watts House originally built one block away in 1799 and moved to this location in 1808. This Federal style home was built by Colonel Demsey Watts. Congressman Henry Clay, Chief Black Hawk and President Andrew Jackson have all been entertained here. When Blackhawk was brought here Captain Watts took him to the Navy Yard to see the battleship New York in Dry Dock 1. Blackhawk commented, “I would like to shake the hand of the man who built that canoe.”
51. 525 North Street
If you are in need of a rest, enjoy the benches in Greenwich Park across the street from the Watts House. If you walk through the park, you will notice a Path of History placard with more information about the yellow fever epidemic. Behind the park, you will see 525 North Street which was built in 1775 by William Pritchard, a wealthy shipbuilder and Merchant Marine captain. The house was used as an orphanage for children whose parents died in the Yellow Fever epidemic of 1855. The official list showed nearly 400 children had passed through the Pritchard House during the ordeal. A large number of them were also taken to the City of Richmond and placed in orphanages there.
Over 1,200 people died between July and October that year when the ship the Ben Franklin discharged bilge water from tropical seas. Despite the fact that the doctors knew the “yellow fever flies” had something to do with the epidemic, it would be half a century before the true vector, mosquitoes, would be identified by Walter Reed in Cuba. In the summer of 1855, the Gosport Shipyard went from having 1,400 employees to only 400 and the government ordered them to make coffins rather than ships. The relatives were so desperate they would fight over the coffins as soon as they were made.
52. Richard Dale Monument
Continue down North Street and as you cross Washington Street, in the median you will see a monument to Richard Dale who was the premier Commandant of one of the nation’s first shipyards, now known as the Norfolk Naval Shipyard in Portsmouth. Dale was born a few blocks to the north at Swimming Point. He was captured five times by the British during the Revolutionary War and escaped all five times. He also served as John Paul Jones’ Second in Command aboard the Bon Homme Richard. When John Paul Jones died he willed the gold hilted sword given to him by the King of France to Richard Dale.
53. Lincolnville Neighborhood
As you continue down North Street, you are in the neighborhood formerly called Lincolnville which was Portsmouth’s first middle-class African American neighborhood developed in 1890. It was a ‘city within a city,’ with its own schools and services.
The last house on the right was the birthplace of Mayor James Holley III, Portsmouth’s first African American Mayor. He was Portsmouth’s longest-serving mayor, spending 18 years in office. He was remembered as a man with a great love for his “Portsmouth Family”. His trademark suits were so well known that he was listed as America’s Best-Dressed Mayor on the cover of Esquire Magazine in September 2007. Notice the Path of History placard that contains more information.
54. Emanuel African Methodist Episcopal Church
Next you will see the Emanuel African Methodist Episcopal Church, founded in 1772, three years before the American Revolution. It is the oldest African American church in the area. Originally the church was on Glasgow Street, but it was “burned by wicked hands” in 1856. This building was built entirely by hand by slaves and free blacks in one year and was dedicated in 1857.
Emanuel also prides itself in being one of the stations on the Underground Railroad, and in it can be seen the hiding places for slaves as well as the location of the water duct used by slaves to crawl to the Elizabeth River so they could stow away on merchant ships. No slave was ever caught in the church.
The church has its original stained glass windows and hand-carved benches and pews. Because mail would not be delivered to African Americans at that time, two gentlemen had post office boxes downtown specifically to receive mail for the members of the congregations so the church also served as a substitute post office for the people living in Lincolnville. If you would like a tour, please call the church secretary at 757 393-2259 between 9 and 3 Monday through Friday to schedule an appointment.
55. Cedar Grove Cemetery
If you stop here in front of the church and look down North Street, you can see the historic Cedar Grove Cemetery which is listed on the Virginia Registry of Historic Sites. Purchased in 1831, it was the first secular cemetery in Portsmouth. It is known for its handsome sculptures, and for the graves of many men and women of national prominence. When it was first established, the keeper was paid $50 a year. In the 1850s a woman took over the job and was paid $10 less per year than the prior keeper. With more than 400 graves that feature notable examples of Greek Revival, Late Victorian, and Exotic Revival funerary art, as well as historic markers, Cedar Grove provides another excellent historical walking tour. The entrance is located on the far side of the cemetery at 301 Fort Lane.
56. 359 Washington Street
Now turn around and proceed back up North Street and make a right turn on Washington Street. Stay on the right side of the street and keep walking until across the street you see the green house, which is the second house from the corner at 359 Washington. This is the Brown-McMurran House built in 1789. It was originally a farmhouse on the highest point of Olde Towne. It once belonged to Thomas Veale, the heir to the city’s founder, Colonel Crawford. The house was originally one room deep and two stories high. Notice the windows on the side of the house. When it was built, glass was very expensive so houses often had tiny windows.
57. 412 Washington Street
Continue down the street one block until you reach 412 Washington, on the right. For many years before the Civil War, the white petticoat was an indispensable garment. Fortunately for the soldiers, a deep hem was the correct finish for these underskirts. Since medicine was in very short supply in the Confederacy, brave women would steal it from the Federal hospital in the Macon House Hotel on North Street by hiding it on the inside of their hems. They would bring it to this home and then hide it under a stone beside the door. Other women would then pick it up and smuggle it through Union lines in their petticoat hems.
58. St. John’s Episcopal Church
Next to this home is St. John’s Episcopal Church. You may notice that the stone looks familiar, you saw it earlier on Court Street Baptist Church. In the early 1830s, seven members of Trinity Episcopal Church had become dissatisfied with the church and decided to form a congregation themselves. They withdrew from the church in 1848 and elected a vestry and built their church which was burned. A new church was built on this site in 1897 designed by Charles Cassell, a local architect and member of the vestry who also built the Art Nouveau home at 328 Court Street.
Among the many treasures of this church is what is thought to be one of the largest windows by Tiffany and Company in the nation. It was placed over the sanctuary and illuminated from the back, since the parish hall, when it was built, blocked the sun from shining through it. Notice that the brass cross facing Washington Street promises “All Seats are Free”. This was because at Trinity, their former church, you had to pay rent for your pew. From 10 am to 1 pm during the week you can ring the bell in the parking lot off London Street and someone will give you a tour of the sanctuary.
59. St. Paul’s School
Turn left on London Street and cross Washington Street going back toward the parking garage.
Across the street, you will see the former St. Paul’s School. Built in 1891 at the bequest of Elizabeth Burke Gregory, this school was operated by St. Paul’s Catholic Church. During its 100 years of service, 13,000 students passed through its doors. Girls were admitted in 1931, and it became Portsmouth’s first integrated school in 1959. Upon closing in 1991, it was one of the oldest Catholic schools in the nation. It was renovated in 2020 and is currently a commercial event venue called Cambridge Hall, named for the square in which it resides.
60. Belgian Block
As you are strolling down London Street, notice the large granite stone blocks used in many driveways. This is called Belgian block and was often used because it gave horses’ hooves better grip than a smooth surface did. Much of this block came here as ballast in ships. All the curbs in Olde Towne are also made of granite.
61. 423 London Street
Continue down London Street for a half of a block until you see 423 London on the right which was built in 1846.
This house was a model for the houses at 419 and 421, both built 40 years later. A Federal-style frame dwelling, it received an Italianate update with the installation of brackets at the cornice line. During the Civil War, it was used as a hospital and later an apothecary shop.
62. 412 London Street
A few houses down on your left you will come to 412 London which is considered one of the oldest homes in Portsmouth, this colonial bungalow was likely built before 1750. During the Union occupation of Portsmouth, the area’s Provost Marshal worked out of this home. It also has an interesting fire mark.
You've done it!
By now you’ll probably recognize this section of London Street and realize that you are only a block away from your starting point at the Middle Street Garage. When you reach the garage, you will have walked a little over two miles and wandered through over 300 years of history!