Welcome Sign - Thirteen year old Matthew Calloway came to the Madison Board of Aldermen October 10, 2002 to request permission to build a new welcome sign for the town of Madison. It was Matthew's desire to design and build this as part of his Eagle Scout project. The sign was completed March 10, 2003.

Boxwoods - circa 1810, is considered the oldest house in Madison. It was built in the Federal style for Randall Duke Scales who in 1812 sold ninety-six one half acre lots which became the original Town of Madison. A spectacular view from the house overlooks the Dan River Bottoms. A long entry walkway bordered with ancient boxwoods lends the house its name. The exterior of the house is a beautiful combination of Federal and Victorian styles which is the result of expansion and alterations during the late nineteenth century. Present owners are descendants of the Vaughn family who purchased the house in the mid 1800's. Nineteenth-century outbuildings include a smokehouse, coal shed and slave quarters.

The Boxley - The complex configuration of the Boxley is the result of three stages of construction. The original one-story cottage with a splayed gable roof and large interior chimney pre-dates the establishment of Madison. It was more than likely built by Edmund Brewer, a previous owner of the property, in 1785.

The earlier portion of the two-story house was erected in 1825 by William Hegwood. It is distinguished by transitional Federal-Greek Revival fluted window surrounds with corner roundels and a two-story porch supported by Tuscan columns.

In the 1840's a two-story Greek Revival, hip-roofed ell with another two-story pedimented porch supported by monumental Ionic columns was added to the south end of the earlier two-story block so that the house now faces Hunter Street. Most of the original Brewer house is no longer standing; however, the portion that does remain is now part of the outside kitchen.

The Twitchell-Gallaway House is in the Academy Street National Register Historic District. It was built for Randall Duke Scales as a wedding gift for his daughter Elizabeth upon her marriage to Joseph Twitchell in 1834. In 1880, the house was purchased by John Gallaway, who started the Bank of Madison and is credited with owning Madison's first bathtub. Extensive renovations sympathetic to the original style and historic integrity were done in the 1990's by Donald Rumsey. The modernized kitchen still in the basement, a spectacular new front porch and beautiful landscaping are interesting features.

The Madison Presbyterian Church was built in 1848. The original building, still used as a sanctuary, is a good example of vernacular Greek Revival style with its pediment gable end to the street. The interior plan consisted of a pulpit at the front so parishioners entered through separate doors to pews divided down the middle of the church to keep them apart. Some time after the Civil War the slave balcony was removed and the pulpit was moved to the back of the church. Sympathetic additions include a 1880's richly textured enclosed portico which contributes to the building's Neoclassical style through its gable with boxed cornice and returns.

The original Presbyterian cemetery is located at 113 W. Academy Street. The cemetery contains the remains of notable residents who helped found the town and established it as a major trading center and tobacco market.

The Pratt House - C.B. Pratt brought his family to Madison in 1892 and lived in the Aiken-Pratt House while this house was built. It stands on one of the original 96 lots platted by Randall Duke Scales and was finished around 1900. Hipped, gabled and conical roofs, Palladian windows in the attic gables and stained glass windows are characteristic of the Queen Anne style. The first Madison Post Office was located in the side yard on the west. The Pratt family maintained ownership until 1995 when a local contractor purchased the property. Renovations included a new foundation, new roof and a striking Victorian paint job. Sitting on a hill overlooking downtown, the Pratt house is an imposing landmark. The house is in the Decatur-Hunter Street Historic District.

Rosemont was built by Nathaniel Pickett, owner of Madison Lumber Company, co-owner of the first automobile agency in Madison, and first chairman of the Madison School Board. Though he had major losses in the crash of 1929 and died soon after with a heart attack at the age of 58, the Pickett family was able to keep the house until the 1960's when new owners conducted renovations which included painting red brick walls cream and the red tile roof green. In the 1980's, the Hayden Lees made sympathetic renovations which included major roof work and painting the brick walls rose. Multiple roof lines columned porches and port cochere, the sun room and the extensive use of Tuscan columns make Rosemont a beautiful example of the Queen Ann style. Interior paneled wainscoting and parquet tile floors are notable features. Rosemont is in the Decatur-Hunter Street Historic District.

Wakeham was constructed in 1921 for Junius C. Brown, a prominent attorney and Madison civic leader. His widow, Eliza Pratt Brown lived to be 90 plus years and remained in the house until her death. The Browns, who had no children, left a prestigious scholarship to Wake Forest University. Recent owners have done cosmetic renovations and installed a new roof. Harry and Nelda Clendinen owned the house for years and were noted for their carefully maintained landscaping and seasonal decorations which are appreciated by the many people who pass daily. Harry passed away and Nelda has recently remarried to Mr. Porter. This high-style balcony, and carved wooden sunburst lunette above the entrance is one of Madison's most beautiful houses. Wakeman is in the Academy Street Historic District.

Town Clock - Madison's memorial for World War I veterans was installed during construction of an automobile dealership owned by Nat Pickett, Stirling Webster, and Jim Vaughn. The cost of the clock was around $600 and it was shipped by boat and rail from Boston. Engraved on the bell and face of the clock are the words "All of those who served" and "Madison, N.C." The clock has been refurbished and remains one of few large clocks operated by winding. In the 1920's, the building was purchased by T.D. Meadow and used as a wholesale grocery company. It is presently used for light-manufacturing by Gem Dandy company. Neo-Romanesque detailing is created by buttresses of gray brick and window arches which have been filled with brick.

Jordan Cabin - The 800 foot square, 2-room log cabin is situated on Plats #1 and #2 of the Town of Madison. A recent find in the chimney of a brick with 1799 etched into it, indicates the cabin is much older than originally thought, probably dating to 1799. Therefore, it was built before the area became a town. Peter Scales owned the land and it was possibly built by him, or his son Randall Duke Scales. R. D. Scales secured 324 acres of land from his father in 1818 and divided a portion of it into 96 half-acre lots.

The large multipurpose room downstairs has a large fireplace with a Federal style pegged mantle. The bedroom was upstairs. The beaded-board finish inside and above average detailing indicate it was built by a person of financial means. Because of the excellent condition of the logs, probably siding was put on at the time of building.

Madison Historic District and Properties Commission acquired the 209 year old cabin in 1998 and is in the process of restoring it to mid l9th century condition when it will be used for demonstrating history and available for touring.

Scale's Law Office - Alfred Moore Scales, born in 1827, was the son of Dr. Robert and Jane Bethel Scales. He graduated from the University of North Carolina at Chapel Hill in 1846 and was admitted to the state bar in 1851. Scales, a direct descendent of the Scales family who founded Madison, came to Madison prior to 1853. He built his law office in 1856 in the yard of the H. H. Staples home. He announced the opening of the law office in an edition of the Rockingham Democrat.

Scales was a Brigadier General in the Army of the Confederacy and was Governor of the State of North Carolina 1884-1889. While in Madison he served as County Solicitor, member of the N. C. House of Commons for four terms, two terms in the U. S. House of Representatives, and Presidential Elector. He was an Elder of the Madison Presbyterian Church until 1867 when he went to Wentworth, and finally to Greensboro. He was the first layman ever elected president of the state synod of the Presbyterian Church.

The law office was in a state of disrepair and in 1979 a movement was begun by the Historic District and Properties Commission to move the building from the original site to Academy Street beside the Presbyterian Cemetery.