The Roundtop Filling Station in Sherwood is one of only two structures in the city to be listed on the National Register of Historic Places.

The Justin Matthews Company built the Roundtop Filling Station in 1936 for the Pierce Oil Company. Pierce Oil was one of the "baby Standards" formed after the U.S. Government’s breakup of John D. Rockefeller’s Standard Oil Company in 1911.

Pierce operated gasoline stations in Arkansas, southern Missouri, western Louisiana, Oklahoma, Texas, and Mexico. In 1936, Pierce Oil contracted the Justin Matthews Company to construct a uniquely shaped gasoline station along U.S. Highway 67. It is believed the structure was designed by Matthews’ company architect, Frank Carmean, and was built by builder C.C. Eubanks.

Wallace David "Happy" Williford, a senior at Jacksonville High School in Jacksonville, and employee at another Pierce-owned station in Jacksonville, was asked by the company to come operate the new service station. Williford agreed and worked at the station before and after attending school. Williford paid men to operate the station for him during school hours, but says it was hard finding men who would only work for $3.50 a week.

For rent, Pierce charged Williford two cents per gallon of gas sold. At first, the station had no electric gas pumps, and Williford and his employees had to hand pump the gas up into the glass bowl before filling each car’s tank.

Around 1940, the Roundtop became a Sinclair station, after the Sinclair Oil Company purchased Pierce Oil. Around this time, electric pumps were installed some time in the early 1950s, Sinclair sold many of their Arkansas stations, including the Roundtop, to the Phillips Petroleum Company, and the station became a Phillips 66 branded station. In the 1970s, the station would become a DX branded station; and at the time it closed in 1981, it was a Sunoco branded station due to Sun Oil Company’s acquisition of DX.

By 1957, Williford had saved up enough money to purchase the station for $8,000. With business booming, Willford would open up another gas station at the foot of the Broadway Bridge in North Little Rock near the site of present day Dickey-Stephens Park. Williford later closed that station and opened another at 914 East Broadway in North Little Rock. During this time, Williford leased the Roundtop to others. He returned to the Roundtop in the mid-1970s and operated it exclusively until he retired and closed the business in 1981.

In 1989, Wayne Ball, a local auctioneer, coincidentally, a former station employee from his youth, conducted the auction of the Roundtop on behalf of Williford. The winning bid was for $8,000. However, the buyer could not come up with the money, so Williford continued to own the building. However, just a couple of years later, George E. Brown, a North Little Rock businessman, purchased the Roundtop from Williford.

Brown planned to renovate the then dilapidated building; however before this could happen, Brown passed away, and, in October 2003, his heirs donated the station to the City of Sherwood, which had annexed the area in 1975.

For years, the gas station-turned-landmark sat abandoned, and, over time, was the victim of vandalism and theft. In the mid-2000s, Becki Vassar, a former member of Sherwood’s City Council, advocated for the restoration of the station and ultimately caused it to be listed on the National Register of Historic Places in 2008.

In 2010, the Roundtop was featured in "The Last Ride," a film about Hank Williams, Sr., directed by Arkansas native Harry Thomasson. The scenes filmed at Roundtop include, several of the Williams character, his young chauffeur, Silas, and his love interest, Wanda.

In January 2013, Sherwood Mayor Virginia Hillman appointed Darrell W. Brown, an employee of the Department of Arkansas Heritage and lifelong resident of Sherwood, to chair the first Sherwood History and Heritage Committee. Brown, along with Kelly Coughlin, Director of Economic Development for the Sherwood Chamber of Commerce, began working to obtain grant money to aid in the restoration of the Roundtop. On May 8, The Historic Preservation Alliance of Arkansas named the Roundtop as one of the most endangered historic sites in the state of Arkansas. On June 5, the City of Sherwood was notified by the Office of Arkansas Governor Mike Beebe that Sherwood had received a $50,000 historic preservation grant for the Roundtop project from the Arkansas Historic Preservation Program to save the structure and rehabilitate it for use as a substation for the Sherwood Police Department.