The courthouse is surrounded by one- and two-story buildings, and each block is split by an alley. The south side of the square, W. Elm Street, possesses the most intact row of historic buildings. The former Citizen’s National Bank (c. 1910) at 50 W. Elm strongly marks the corner with a monumental limestone portico of paired fluted Tuscan columns supporting a tall entablature and pediment.
The Old Rock Saloon (1876) at 58 W. Elm, with a facade of cut stone and side walls of irregularly sized stone, is the oldest commercial structure in Hillsboro and is unusual because early buildings were built of brick. The saloon, originally owned by town mayor J. E. Ballard, had a gambling hall on the second floor and a cockfighting pit out back. The stucco concealing the first-floor stonework and the wood storefront are from renovations in 1981 under the Texas Main Street program. The alley between the saloon and the brick T. B. Bond Pharmacy (1881; 60 W. Elm) is a Recorded Texas Historic Landmark, Bond’s Alley, noted as the “local site of politics, peddlers’ shows, whittling, cockfights, and fisticuffs.”
The Colonial Trust Company (formerly Farmer’s National Bank) built c. 1885 at 68 W. Elm was remodeled in 1913 with two monumental Ionic columns in antis framing the narrow facade, a complex stack of door and transom, a projecting compound cornice, and an arched window, all framed in limestone and contrasting with the red brick walls.