Tobin Hill, to the north of the city core, is one of San Antonio’s inner neighborhoods located just north of I-35, between Huisache to the north, Highway 281 to the east, and San Pedro Avenue to the west. In Spanish times this area between the San Antonio River and San Pedro Springs provided good agricultural land. Early San Antonio settlers dug irrigation ditches or acequias for irrigation of crops. A major acequia, the Upper Labor, was completed in 1777 and was located at what is now the southern boundary of Tobin Hill. It began at the west side of the San Antonio River headwaters and followed the Rock Quarry Road (now St. Mary’s Street) before it skirted Tobin Hill and flowed into the San Pedro Ditch near Laurel Street and Interstate-35. The land abutting the acequia was distributed by lottery, and the land north of the acequia was parceled out during the latter part of 1777. Due to its value as agricultural land, no real development occurred in the area for another 100 years. An exception, however, was a house built for the overseer of the acequia, which may be the small stone building at 305 E. Euclid Street today.

As the years passed, this part of the city became known as the Old Main Association, and the land was sold to the Maverick family, Gillum & Yongue, and other large landholders. Part of the area now known as Tobin Hill was the result of an 1876 lawsuit between Gillum & Yongue and the City. In a lawsuit the City had misinterpreted the amount of land in a labor (seven acres inside city limits, but 177 acres outside city limits) and awarded Gillum & Yongue 177 acres. When the mistake was realized, the City sued but did not win back the land. Gillum subdivided the 177 acres into lots, donated two blocks on either side of Main Avenue to the City for what is now Crockett Park, and sold the remaining lots, which became known as Gillum Addition.

During the 1880s and 1890s, when members of the Tobin family built seven homes in the area, the Old Main Association and Gillum Addition became known as Tobin Hill. Unfortunately, none of the Tobin houses exist today.

Public transportation in San Antonio, which played a large role in early neighborhood development, began in 1878 with a streetcar route from Main Plaza north to San Pedro Park. Colonel Augustus Belknap owned the system which consisted of mule-drawn cars, and a mule barn was located on the present site of San Antonio College. The first electric trolleys appeared in 1890, with a car barn replacing the mule barn. By 1919 the eastern part of Tobin Hill, anchored by the Pearl Brewery, was served by a streetcar that ran from Dallas St. to King’s Court in the vicinity of Brackenridge Park.

Wherever streetcars went, development followed and spread. Commercial development occurred along the main streetcar corridors, including San Pedro, McCullough, and St. Mary’s Street. Residential development nearby served the needs of those who worked in the businesses. Business owners built large houses, such as those at 130 Lewis Street, 421 Howard Street (now the Victorian Lady Inn), and the Otto Koehler House at 310 W. Ashby Place (now on the campus of San Antonio College). Workers at the Pearl Brewery, established in 1886 on the east side of Tobin Hill, built smaller bungalows within the vicinity.

The architecture was true to the period with many holdovers from the late Victorian era, numerous Craftsman bungalows, and later Colonial Revival and English or Tudor style residences as well as four-squares. The Clegg-Henning House (L.B. Clegg House) at 123 W. Park Avenue is a good example of Spanish Revival architecture. The Aurora Apartments, on Howard Street at Crockett