One-Page Summary

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Click the name of the house to go to it's walking tour page.
1. 335 Main Street - Hattie Drummond House (Visitor Center) (circa 1865).  This house was built for Hattie Drummond by her brother, Mr. Watson, to serve as a millinery business shortly after the Civil War.  Hattie's husband was apparently an irresponsible roamer, guilty of long and frequent absences.  Hattie's brother wanted to provide her with some financial security.  The business proved to be so successful that by 1868 Hattie had paid back her brother, and the house and business were deeded to her "free from all marital rights of her husband".
2. 07040005.jpg (217010 bytes) 203 Main Street - Jordan House (circa 1830) This house was built for Watson P. Jordan about 1830 on the site of a much older home.  It was the home of J.P. Andrews from 1876 to 1922, and later the home of Dr. Rae Parker who practiced medicine in Smithfield from 1922 until his death in 1948. After sitting vacant for over 30 years and falling into great disrepair, the house was restored by Mr. Jeff Stark.
3. Mary_Jackson_House.jpg (39432 bytes) 113 South Mason Street - Mary Jackson House (circa 1760)This house was built by Mary Jackson, a single woman from Scotland, in 1760.  Mary lived for only six months after the house was built.  Originally the house was a two-story Dutch-roofed colonial building, consisting only of the sections on the right side of the porch.  The section on the left was added in 1790, but the construction materials date to the same period as the original house, suggesting that the addition was formed from a portion of a pre-existing structure from another site.  Two shed rooms were added to the rear of the house in the mid 1800's.  These rooms were expanded to a second level in the 1930's.
4. 06260003.jpg (43677 bytes) 112 South Mason Street - Miles Cary House (circ. 1800)Before 1800, this two-story federal style residence was added to a small Dutch-roofed house, which was later moved to the back of the lot and was eventually torn down. The house was restored between 1997 and 2003 by Trey Gwaltney.
5. Trinity Methodist Church Cedar Street & South Mason Street - Trinity Methodist Church (circ. 1898)This Gothic structure, built in 1898, replaced an earlier frame church.
6. Smithfield_Academy.jpg (45426 bytes) 205 South Mason Street - Smithfield Academy (circ. 1826)The building was erected in 1826 as a private school for young men.  After 1872, it became a public school and later a Masonic Lodge.  Restored in 1963, it is used by the Trinity United Methodist Church.
7. Wills-Lightfoot-Folk House 213 South Mason Street - Wills-Lightfoot-Folk House (circa 1752)The Dutch-roofed section was built before 1752 when it was bought by Mr. Wills.  In 1821, Bartholomew Lightfoot added the two-story Federal style annex.  The William Folk family owned the house for 110 years.
8. Hill Street Baptist Church 110 Hill Street - Hill Street Baptist Church (circa 1832)The church was built about 1832 by the Baptists.  Two other congregations have since used this church.
9. Chapman House 130 South Church Street - Chapman House (circa 1892)This house was built around 1892 in the typical Victorian style.  It was remodeled in the 1930's to its present hipped-roof Georgian style.  Once used as the town's bakery, and later as a library.
10. 02020008.jpg (43387 bytes) 212 South Church Street - Delk House (circa 1877)This house was built in 1877 for Captain O.G. Delk of Kemper's Brigade in the Civil War.  Delk was later captain of one of the steamboats serving the port of Smithfield.  The house features floor-length windows.
11. Eason-Whitley House 220 South Church Street - Eason-Whitley House (circa 1756)This house stands on one of the first lots to be sold in the new town of Smithfield in 1752.  The lot sold for four pounds, six shillings.  James Eason first occupied the home in 1756.  It was the home of the Whitley family from 1913-1988.
12. 02020014.jpg (41678 bytes) 226 South Church Street - Pembroke Decatur Gwaltney House (circa 1876)Victorian in style, the house was built in 1876.  Mr. Gwaltney founded the peanut business in Smithfield and later re-established the meat curing business started by Mallory Todd.
13. WIndsor Castle 301 Jericho Road - Windsor Castle (circa 1750)Built about 1750 by Arthur Smith IV, founder of Smithfield.  The home is a stucco-covered brick home with dormer-windowed second floor and a full basement.  It is, most likely, not the original house of the plantation which was patented in 1637 to the third son Arthur Smith of Blackmore, Essex, England.  The town of Smithfield was laid out on a portion of Smith's original land grant from the king of England.  The town of Smithfield was named for this Arthur Smith.
14. P.D. Gwaltney House (Second) 304 South Church Street - Pembroke Decatur Gwaltney House (circa 1901)This house is the epitome of the Queen Anne style of Victorian architecture.  The house, completed in 1901, took two years to build with its turrets, towers, gables, stained-glass windows, bay windows, tiled roof, porte-cochere, and cabinet mantles (inlaid in mother of pearl).  In 1926, P. D. Gwaltney Jr., along with A.S. Johnson, worked hard to get the Smithfield Ham recognized.  On page 1001 of the Acts of the General Assembly, Section 23, is the first law dealing with the famous Smithfield hams.  Strict rules were made about labeling hams, shoulders, sides and jowls.  The penalty of violation of this act was set at not less than $25 or more than $300.  The house remains in the P.D. Gwaltney Family.
15. 02020029.jpg (52667 bytes) 334 South Church Street - Goodrich House (circa 1886)This house was built about 1886.  It is elegantly Victorian and is distinguished as the only home in Smithfield with a Mansard roof and stained-glass cupola.
16. wpe14.jpg (43800 bytes) 338 South Church Street - Andrew Mackie House (circa 1796)Built about 1796, this house features a beautiful colonial-style garden sloping to Little Creek, with boxwood bushes, a gazebo, and Chippendale benches.
17. wpe8.jpg (39433 bytes) 352 South Church Street - Thomas Blow House (circa 1800)Part of this house is believed to have been built as early as 1800 by Thomas Blow.  Later in 1827, the widow of General Francis M. Boykin (for whom Fort Boykin is named) resided here.  General Boykin served with both General Washington and Patrick Henry during the Revolutionary War.
18. wpe1B.jpg (26968 bytes) 373 South Church Street - Benjamin Drew Brick Fireproof Storehouse (circa 1810)
19. wpe12.jpg (29839 bytes) 357 South Church Street - Wilson-Morrison House (circa 1771 & 1778)Facing the house, the right wing dates to 1771 and the left wing to 1778.  It features a free-hanging stairway in the entry foyer.
20. wpe16.jpg (46000 bytes) 351 South Church Street - Watson P. Jordan House (circa 1822)Originally built circa 1822 by Watson P. Jordan, this house was purchased by the Honorable Archibald Atkinson in 1837.  Atkinson was the U.S. Congressman for the local district from 1839-1844 and Mayor of Smithfield from 1852-1855.
21. wpeA.jpg (47464 bytes) 345 South Church Street - Berryman House (circa 1900)This is one of the last and most impressive homes of the Victorian period in Smithfield.  It features a ballroom on the third floorn a widow's walk at its peak, and an ornate gazebo overlooking the Pagan River.
22. wpeC.jpg (45341 bytes) 335 South Church Street - Sinclair House (circa 1758)The original part of this home is believed to have been built by Andrew Mackie after he purchased the lot in 1758.  Mackie and his family occupied the house until 1778, when he sold it to Captain John Sinclair.  Sinclair occupied the house from 1778-1796.  He was a colorful character who was the captain of a blockade runner during the Revolutionary war.  As a blockade runner, he would secretly maneuver his ships through the blockade of British warships in order to bring in supplies to the colonists.  After the war, he operated as a privateer against British trade ships.
23. wpe10.jpg (41329 bytes) 309 South Church Street - William D. Folk House (circa 1876)Built in 1876 and painted red during Victorian times, this was the home of William Folk, Mayor of Smithfield, from 1884-1893.  Since that time it has been the home of two more of Smithfield's mayors - Howard W. Gwaltney (1950-1961) and Smithfield's first woman mayor, Florine H. Moore, elected in 1986.
24. 02020006.jpg (55195 bytes) 213 South Church Street - King-Atkinson House (circa 1798)This home was built by Thomas King who was an ensign in the Revolutionary War.  It was later owned by Capt. Joseph Atkinson who served in the militia in the war of 1812.
25. wpeE.jpg (44733 bytes) 201 South Church Street - The Cottage (circa 1887)This house was built around 1887 of board and batten construction in the American Gothic Style.
26. wpe1D.jpg (43077 bytes) 123 South Church Street - Wentworth-Grinnan House (circa 1780).  The left wing of this house dates to 1780.  It was known as the "little storehouse".  The two-story right wing was added in the 1820's or 1830's.
27. 02020001.jpg (64380 bytes) 117 South Church Street - Wentworth-Barrett House (circa 1752).  This house was one of the first buildings to be erected in 1752 in the new town of Smithfield. It was the residence of Captain Samuel Wentworth. It stood unoccupied for more than forty years before being restored by Fred M. Barrett II in the 1950s.
28. 07040037.jpg (112783 bytes) 111 South Church Street - Christ Episcopal Church (circa 1830).  The church was built in 1830.  The church bell is said to have been tendered to the Confederate Ordinance Department in 1862 during the Civil War.
29. 07040033.jpg (206425 bytes) 22 Main Street - Todd House (circa 1753).  The left wing of the house was built circa 1753 by Nicholas Parker, a cabinet maker.  It was later the home of Captain Mallory Todd, who was born in Bermuda and was living in Smithfield by 1767.  Mallory Todd is the first documented person to have cured and exported Smithfield hams.
30. 07040031.jpg (41421 bytes) 36 Main Street - Thomas House - "Mansion on Main" (circa 1889).  The house was built about 1889 for Richard S. Thomas, a prominent Smithfield lawyer and historian.  It sits on the site of an earlier house.  The house is now a bed and breakfast called "Mansion on Main".
31. 07060003.jpg (187980 bytes) 103 Main Street - Isle of Wight County Museum (circa 1913).  The building was built in 1913 to house the Bank of Smithfield, which had outgrown a previous building.  It features imported marble and tile and an enormous Tiffany style domed skylight.  Since 1978 it has been the home of the Isle of Wight County Museum.
32. 07040027.jpg (47965 bytes) 112 Main Street - Smithfield Inn (circa 1752)The Smithfield Inn was built in 1752 for Henry Woodley.  It was first opened as a tavern by William Rand in 1759 and has been used in that capacity for over half of its existence.  It was bought by Christ Episcopal Church in 1854 for use as a rectory until 1892.
33. 07170010.jpg (190811 bytes) 124 Main Street - Gaming House (circa 1766)This building was in use as a counting house and gaming house by 1766.
34. 07040002.jpg (230121 bytes) 130 Main Street - Old Courthouse & Clerk's Office (circa 1750)This building was built in 1750 and used as a courthouse until 1800 when the court was moved to Isle of Wight County Courthouse.  After that time, it was converted to a private three-story dwelling.  The private dwelling was constructed in such a way that the original structure of the courthouse was preserved almost completely intact.  In 1959 the Isle of Wight branch of the Association for the Preservation of Virginia Antiquities began restoration of the building to its original form.  It is now open to the public with no charge for admittance.  The adjoining clerk's office was built in 1799 and has been used as an office or a shop since 1800.
35. wpe8.jpg (31692 bytes) 106 North Mason Street - Old Jail (circa 1799)The jail was built in 1799 by Isaac Lever, a contractor.  It was used as a jail for only one year until the courthouse was moved.  Since 1800 is has served primarily as a residence.
36. 07120074.jpg (198517 bytes) 220 Grace Street - The Grove (circa 1780).  The Grove was built between 1780-90 for Thomas Pierce.  This brick residence once stood in a grove of oak trees, which was cut down and sold to the Russian Navy during the Crimean War.  The building was once used as a boarding house and a hotel.  It was restored in 1956 by Lieutenant Governor and Mrs. A.E.S. Stephens.
37. 07120077.jpg (41217 bytes) 222 Grace Street - Hayden Hall (circa 1812).  Hayden Hall was built for Mrs. Martha Hall sometime before 1812.  The house was used briefly in 1836 for the first girls' school in Smithfield.  The small park across the street was originally the entrance lane to Hayden Hall.
38. 07120079.jpg (42305 bytes) 204 Grace Street - Oak Grove Academy (circa 1836).  This building was built in 1836 as "Oak Grove Academy for Young Ladies".  It has also housed two other institutions of learning, The Smithfield Female Institute ; and The Smithfield Male and Female Institute.
39. 07120082.jpg (202659 bytes) 308 Grace Street - James Robert Jordan House (circa 1907)This handsome home was built in 1907 and was later converted into apartments in the thirties.  It is now a single residence.
40. wpe6.jpg (35223 bytes) 320 Grace Street - The Cottage (circa 1885)This beautifully restored home was built in 1885 for Mrs. Sally Eley, owner of the Smithfield Female Institute.
41. wpe4.jpg (20134 bytes) Grace Street - Pierceville (circa 1730).  A fine Dutch-roofed house built around 1730 for Thomas Pierce, a merchant and a leader in the fight for Independence.
42. wpe2.jpg (37356 bytes) 108 Cary Street - Pollard House (circa 1750).  Built between 1750 - 1780 on Main Street, this house was moved around the corner to Cary Street about the turn of the century.
43. 06260028.jpg (201460 bytes) 336-346 Main Street - Victorian Row (circa 1900)Victorian row , also know as the Painted Ladies, consists of five typical houses of the late Victorian time period (early 1900's), each featuring bay fronts and gingerbread trim.  The houses were built around 1901 by Burton W. Hearn, who, himself, lived at 346 Main Street.
44. 06260038.jpg (217118 bytes) 345 Main Street - Britt-Simpson House (circa 1854)Built around 1854 by George W. Britt, this was the home of Frank B. and Emily Delk Simpson.  Mrs. Simpson was one of the founders of the Women's Club of Smithfield and the organizer and first director of the Isle of Wight Branch of the Association for the Preservation of Virginia Antiquities (APVA).

Four ways to tour Historic Smithfield

  Chronological Order    Stop-By-Stop 
  One Page Summary   

  Large Map 

  A Brief History of Smithfield 

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Adapted from the original hard copy walking tour designed by the Smithfield & Isle of Wight Convention & Visitors Bureau.
For additional information about the walking tour, contact the Visitors Bureau at: 757-357-5182 or 800-365-9339.
Unless otherwise noted, the homes shown on this site are private residences and are not open to the public.

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