The first Sussex County Courthouse situated on The Circle was completed in 1793 after the County Seat was moved from Lewes to Georgetown. In 1837, that Courthouse was moved a short distance from The Circle onto Bedford Street so a new larger brick courthouse could be built on the same grounds. The original Courthouse was restored in 1976 and is still used occasionally for special functions. Also of historic interest, the original whipping post remains in place on The Circle.

The present Sussex County Courthouse was completed for use in 1840 and remains in service to this day. The Courthouse has undergone several renovations and additions with the last one completed in 2006. The Courthouse is listed on the National Register of Historic Places and all renovations have strived to keep the historic feel to the building.

While the Courthouse and The Circle are the center of many community activities, by far the most famous and unique event is known as Returns Day. Returns Day occurs every two years on the Thursday after the General Election in November. In days gone by, the town crier would read the results from the balcony in front the Courthouse, which was the first time the citizens would know the outcome of the elections. That tradition continues to this day, after which the candidates participate in a ceremonial "burying of the hatchet." The day is also highlighted by a parade in which the candidates ride in horse drawn buggies (which are housed at all other times in the Nutter Marvel Museum on South Bedford Street) with the winning candidates sitting facing forward in the buggy.