The story of the Surry, Sussex & Southampton Railway began on February 16th, 1886, when the Commonwealth of Virginia approved a charter for the construction of a 36 inch narrow gauge common carrier railroad between a point on the south shore of the James River, into the virgin yellow pine forests of Surry, Sussex, Southampton, and Isle of Wright counties. Through a majority stock ownership, the Surry Lumber Company would finance and construct the railroad as well as purchase rolling stock for the railway to use. The Surry Lumber Company itself was owned by R. T. Waters & Sons of Baltimore, Maryland, which operated the company as one of their many subsidiaries.

Construction of the railroad began in April of 1886 from a sawmill located near Mussel Fork Plantation, Virginia, northward to Scotland's Wharf, Virginia. By 1896, a new town had sprung up around the sawmill with the name of Dendron. Dendron was the location of the Surry Lumber Company's sawmills and was the operating headquarters of the railroad's owners through the company's entire existence. The northern terminus of the line, Scotland's Wharf was located on the James River reasonably close to the historic village of Jamestown. Due to this convenience, the railroad utilized passenger service to transport visitors to the wharf where they would then board a ferry for the short trip to Jamestown Island.

The history of the Surry Lumber Company is one that lived and died with the railroad. Originally incorporated in 1873 by David Steele, a carpetbagger from New Jersey, the company would go on to cut and manufacture timber on land purchased from the estate of Major William Allen. This 1,000 acres or so was once a part of Major Allen's extensive Claremont Plantation. For lumber transport, the company originally utilized mule power on a strap iron tramway constructed from a sawmill on the Blackwater River near Mussel Fork Plantation, to Sloop Point, Virginia, near the town of Claremont, Virginia. At the same time the tramway was being built, the Commonwealth of Virginia approved a charter for the Atlantic & Danville Railway's James River Division from James River Junction, Virginia, to Claremont. This, and other financial incentives, led the Surry Lumber Company to incorporate a common carrier railroad to operate the tramway. Officially chartered as the Surry County Railroad & Lumber Company, this railroad was planned to interchange and operate with the similarly narrow gauge Atlantic & Danville Railway. The railroad's charter was officially approved on April 21st, 1882, however, before any improvements were made on the tramway, the railroad, along with the Surry Lumber Company, defaulted on loan payments and all of the enterprise's assets were transferred over to the original investors of the company; R. T. Waters & Sons of Baltimore, Maryland. To protect their investment, R. T. Waters & Sons decided that instead of liquidating the company and it's railroad, a new company would be formed and hopefully would fare better than the aforementioned predecessor. Thankfully, R. T. Waters being an investment based firm had plenty of money to spare and could invest some into the finance stricken enterprise.

On the 3rd of January, 1885, R. T. Waters & Sons incorporated the "new" Surry Lumber Company to operate lumber related businesses in Surry, Sussex, Southampton, and Isle of Wright counties. This company would inherit all properties previously owned by David Steele including 1089.25 acres of timber land, a 36" inch narrow gauge tramway constructed with strap iron tracks, and one 36" inch gauge locomotive. Immediately after the corporate reorganization, R. T. Waters & Sons decided to abandon the tramway between Dendron and Sloop Point in favor of a new, more direct route, to the James River. This is where the Surry, Sussex & Southampton Railway comes into play as the railroad was going to be the main form of transport between the mill and outside markets. The railroad would also deliver freshly cut timber directly to the mill using temporary light rails built into company owned lumber tracts. These temporary branch lines would be operated by light 0-4-2T "Dummy" locomotives to limit weight.

Interestingly, David Steele, the original incorporator of the first Surry Lumber Company, actually became an employee of the R. T. Waters & Sons owned Surry Lumber Company and served as a woods boss. Ironically for Steele, on July 6th, 1888, he became the Surry, Sussex & Southampton Railway's first fatality when he was crushed by a locomotive while in the woods.

Back to the construction of the Railroad, the wharf at Scotland's Wharf was finished by the end of 1886 and was considered by engineers nationwide as one of the most modern and structurally sound industrial piers ever constructed. The thirteen mile line from Dendron to Scotland's Wharf was completed by December of 1886, but the railroad company desired for an interchange to maximize competition. This led the directors of the railroad to draft a survey to extend the railroad south seven miles to the town of Wakefield, Virginia, to interchange with the Norfolk & Western Railway. Construction had finished by June of 1889 and trains were now able to transport cut lumber to either the Norfolk & Western at Wakefield, or for marine traffic via the company's wharf at Scotland's Wharf.

The railroad continued construction beyond Wakefield to reach newly purchased timber tracts around the town of Dory, Virginia. Interestingly, the railroad decided against crossing the N&W at grade and so constructed a tunnel underneath the Norfolk & Western to reach the new lumber town of Dory. Dory remained the southern terminus of the railroad's main line until the line was extended to Vicksville, Virginia, in 1904. The railroad served many different logging camps created by the Surry Lumber Company including Dory, Straw Hill, Upson, Central Hill, and Vicksville. As the available lumber around the camps were depleted, the Surry Lumber Company began to dismantle the camps and move them to other areas. Dory was no longer in use as a lumber camp in 1904, however the community continued to be served by the railroad until the end. The logging camp at Straw Hill was abandoned in 1907, while the camp at Upson was no longer in use in 1915. The last two logging camps in operation, Vicksville and Central Hill, were finally abandoned with the liquidation of the Surry Lumber Company in 1927. In 1907, the railroad's main line was extended for the last time from Vicksville, to the town of Sedley, Virginia. Sedley was located on the Virginian Railway and so served another potential interchange partner. The town also became the headquarters for all lumber transport related businesses for the Surry Lumber Company. This included the Surry, Sussex & Southampton Railway.

Production peaked around 1920 after the end of World War One and began to slowly decrease. By 1925, the Surry Lumber Company had exhausted all of it's lumber holdings and began to lose money on the mills at Dendron and the Surry, Sussex & Southampton Railway. One reason for this economic downward spiral was that the Surry Lumber Company never replanted seedlings on cleared land and so was left with worthless stumps which couldn't be sold. Due to this economic downturn, R. T. Waters & Sons, the long time owner of the railroad and the Surry Lumber Company, made the somber decision to permanently close the mills at Dendron with the final logs being cut on October 27th, 1927.

With the lumber mills closed, the Surry, Sussex & Southampton Railway was operating on borrowed time as the sawmills were it's major customer. Surprisingly, the company continued to be operated by R. T. Waters & Sons almost three years after the mills were closed. The final train ran in July of 1930, and all the tracks were torn up and sold by the end of the year.

For being an industrial oriented narrow gauge common carrier railway abandoned in the 1930's, quite a few pieces of rolling stock have survived into preservation. Two steam locomotives, #6 and #26, have both survived with #6 currently in operation at the Midwest Central Railroad in Iowa. Infrastructure wise, the right of way is still pretty evident for those who know what to look for. However, many former lumber camps such as Straw Hill and Upson have vanished completely. Dendron is now a sleepy residential community leading many to never guess that this quiet town was once associated with the largest yellow pine lumber company in the United States of America.