Several vintage gas stations at the northeast corner of the courthouse square and on the main highway through Hillsboro illustrate the rapid dominance of auto transportation in the decades just before and after World War I. Grimes Garage is an early urban garage type. The tall, one-story brick facade aligns with its neighbors, but most of the lower part of the building is open as an angled drive-through. The remaining L-shaped building contains office, showroom, and shop areas. Window surrounds within the drive-through are trimmed with orange, black, and white glazed tiles in geometric patterns. Auto mechanic Fred O. Grimes was a promoter of auto service and worked on Texas State highway commissions to establish paved roads across Texas. His first garage venture in 1906 failed because there were too few vehicles in the county to support the business.
The former Sinclair Service Station (1930s) diagonally opposite at 113 N. Waco (now a restaurant) followed the company standard Mission design, with white stucco walls, a green tile roof, and scroll brackets under the ends of lintels. At N. Waco and Franklin Street, the former Gulf Service Station (1930s) is a low, rectangular block with a fully glazed corner office and a thin canopy forming an ell.